Query

Query Results Date

1. Query
S O

O NH

22 reactions in Reaxys

2013-09-26 05h:24m:45s (EST)

Search as: Product, As drawn, No salts, No mixtures

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OH

O H 2N S O

HN

S O

Rx-ID: 28249269 View in Reaxys 1/22 Yield 87 % Conditions & References Example Title General experimental procedure for N-alkylation of amides General procedure: To a mixture of an alcohol (1.0 mmol) and an amide (1.2 mmol) in 1,4-dioxane (2 ml) HClO4*SiO2 (50 mg) was added. The mixture was stirred at 80 C and the reaction was monitored by TLC. After completion the mixture was filtered to recover the catalyst and the residue was washed with EtOAc (3 .x. 5 ml). The combined organic portion was subjected to column chromatography (silica gel, hexane-EtOAc) to obtain a pure Nalkylated amide. With perchloric acid adsorbed on silica gel in 1,4-dioxane, Time= 3h, T= 80 C Das, Biswanath; Reddy, Parigi Raghavendar; Sudhakar, Chithaluri; Lingaiah, Maram; Tetrahedron Letters; vol. 52; nb. 27; (2011); p. 3521 - 3522 View in Reaxys 66 % With 12-phosphotungstic acid, Time= 4h, T= 140 C Wang, Guan-Wu; Shen, Ye-Bing; Wu, Xue-Liang; European Journal of Organic Chemistry; nb. 25; (2008); p. 4367 - 4371 View in Reaxys
2H

NH O O S

S O

NH

Rx-ID: 8878110 View in Reaxys 2/22 Yield 80 % Conditions & References Stage 1: With 2,2,6,6-tetramethyl-piperidine, n-butyllithium, potassium tert-butylate in tetrahydrofuran, hexane, T= -78 C , Inert atmosphere Stage 2: With methanol-d4 in tetrahydrofuran, hexane, Inert atmosphere, regioselective reaction Fleming, Patricia; Oshea, Donal F.; Journal of the American Chemical Society; vol. 133; nb. 6; (2011); p. 1698 - 1701 View in Reaxys Stage 1: With n-butyllithium, potassium tert-butylate in tetrahydrofuran, T= -78 - 20 C Stage 2: With methanol-d4 in tetrahydrofuran, T= 20 C , Further stages. MacNeil, Stephen L.; Familoni, O. B.; Snieckus, Victor; Journal of Organic Chemistry; vol. 66; nb. 11; (2001); p. 3662 - 3670 View in Reaxys

O S
O S O O O S NH 2 N O

O O O S NH 2

NH

HN

S O

Rx-ID: 10348417 View in Reaxys 3/22 Yield Conditions & References 59 %, 25 % With [bis(acetoxy)iodo]benzene, magnesium oxide, dirhodium tetraacetate in dichloromethane, Time= 6h, T= 40 C Toumieux, Sylvestre; Compain, Philippe; Martin, Olivier R.; Selkti, Mohamed; Organic Letters; vol. 8; nb. 20; (2006); p. 4493 - 4496

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View in Reaxys

NH O O S

2H

HN

S O

Rx-ID: 8878109 View in Reaxys 4/22 Yield 94 % Conditions & References Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 0.5h, T= 0 C Stage 2: With methanol-d4 in tetrahydrofuran, hexane, Time= 1h, T= 0 C , Further stages. MacNeil, Stephen L.; Familoni, O. B.; Snieckus, Victor; Journal of Organic Chemistry; vol. 66; nb. 11; (2001); p. 3662 - 3670 View in Reaxys

O H 2N S O

NH 2

HN

S O

Rx-ID: 31489996 View in Reaxys 5/22 Yield 93 % Conditions & References in water, ethyl acetate, T= 0 - 20 C , Inert atmosphere Schneider, Cedric; Broda, Ellen; Snieckus, Victor; Organic Letters; vol. 13; nb. 14; (2011); p. 3588 - 3591 View in Reaxys

O S N O

NH 2

HN

S O

Rx-ID: 25050864 View in Reaxys 6/22 Yield Conditions & References Example Name 4 Example Title Preparation of N-ethyl Toluenesulfonamide EXAMPLE 4 Preparation of N-ethyl Toluenesulfonamide A 1 liter flask equipped as for Example 3 was charged with 3.5 moles (407.8 gms) of chlorosulfonic acid, and 1.0 mole (92.1 gms) of toluene was added over a 1/2 hour period under N2 at 25 C. to 30 C. Stirring and cooling with an external cold water bath was required. The reaction mixture was then stirred at 25 C. under N2 for 4 hours. The resulting crude sulfonyl chloride mixture was added to a solution of 1.0 mole of ethylamine and 294 gms of NaOH in 900 ml of deionized water at 45 C. to 55 C. over a 2 hour period. The mixture was stirred at 55 C. and at a pH above 10 for 1 hour after the addition was completed. After standing overnight, the organic phase was separated, washed with water, decolorized with potassium permanganate and sodium meta bisulfite, washed with sodium carbonate solution and water, and dehydrated at 125 C. and 0.2 mm Hg (26.66 Pa), giving 123g (61.7percent yield) of light yellow liquid. Proton NMR in CDCl3 was consistent with the N-ethyl toluene sulfonamide structure. GC analysis showed 43.5 percent ortho and 53.3 percent para-N-ethyl toluene sulfonamide plus 2.4 percent tolyl sulfones. With chlorosulfonic acid, sodium hydroxide in water, toluene Patent; Akzo America Inc.; US4713489; (1987); (A1) English View in Reaxys

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NH 2

O S O Na +

HN

S O

Rx-ID: 35635816 View in Reaxys 7/22 Yield 90 % Conditions & References With copper(ll) bromide in dimethyl sulfoxide, Time= 24h, T= 100 C , Inert atmosphere, chemoselective reaction Huang, Liangbin; Jiang, Huanfeng; Qi, Chaorong; Tang, Xiaodong; Wu, Wanqing; Wu, Xia; Chemical Communications; vol. 49; nb. 54; (2013); p. 6102 - 6104 View in Reaxys

O
O H 2N S O

O S

HN

S O

Rx-ID: 32892750 View in Reaxys 8/22 Yield Conditions & References With silver tetrafluoroborate, dibromo[1,3-dihydro-1-(2-pyridinyl)-3-(2,4,6-trimethylphenyl)-2H-imidazol-2-ylidene]platinum(II) in PhNO2-d5, Time= 26h, T= 20 - 150 C , p= 4125.41Torr , Inert atmosphere Cao, Peng; Cabrera, Jose; Padilla, Robin; Serra, Daniel; Rominger, Frank; Limbach, Michael; Organometallics; vol. 31; (2012); p. 921 - 929 View in Reaxys

O S N HO

HN

S O

Rx-ID: 12120570 View in Reaxys 9/22 Yield Conditions & References Reaction Steps: 2 1: ClSO2NH2; pyridine / CH2Cl2 / 0 - 20 C 2: 25 percent / PhI(OAc)2; MgO / Rh2(OAc)4 / CH2Cl2 / 6 h / 40 C With pyridine, [bis(acetoxy)iodo]benzene, amidosulfonyl chloride, magnesium oxide, dirhodium tetraacetate in dichloromethane Toumieux, Sylvestre; Compain, Philippe; Martin, Olivier R.; Selkti, Mohamed; Organic Letters; vol. 8; nb. 20; (2006); p. 4493 - 4496 View in Reaxys

O O S Cl

MeMgHal
HN S O O

Rx-ID: 12152953 View in Reaxys 10/22 Yield Conditions & References Reaction Steps: 3 1: acetone; H2O / 20 C 2: ClSO2NH2; pyridine / CH2Cl2 / 0 - 20 C 3: 25 percent / PhI(OAc)2; MgO / Rh2(OAc)4 / CH2Cl2 / 6 h / 40 C

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With pyridine, [bis(acetoxy)iodo]benzene, amidosulfonyl chloride, magnesium oxide, dirhodium tetraacetate in dichloromethane, water, acetone Toumieux, Sylvestre; Compain, Philippe; Martin, Olivier R.; Selkti, Mohamed; Organic Letters; vol. 8; nb. 20; (2006); p. 4493 - 4496 View in Reaxys

F
(v4)

F B
(v5)

O
O

O S

H 2N

S O

HN

S O

Rx-ID: 32659048 View in Reaxys 11/22 Yield Conditions & References 63 %, 23 % in 1,2-dichloro-ethane, Time= 48h, T= 110 C , sealed tube Chen, Jiayan; Dang, Ling; Li, Qiang; Ye, Yong; Fu, Shaomin; Zeng, Wei; Synlett; nb. 4; (2012); p. 595 - 600 View in Reaxys 54 %, 10 % in 1,2-dichloro-ethane, Time= 24h, T= 90 C , sealed tube, Inert atmosphere Chen, Jiayan; Dang, Ling; Li, Qiang; Ye, Yong; Fu, Shaomin; Zeng, Wei; Synlett; nb. 4; (2012); p. 595 - 600 View in Reaxys

O O O S O N N Cl Cl N S N O

NH 2

HN

S O

O
NH

Cl

Rx-ID: 9016840 View in Reaxys 12/22 Yield Conditions & References 53 %, 35 % in tetrahydrofuran, Time= 4h, T= 20 - 22 C Kweon, Deok-Heon; Kim, Ho-Kyun; Kim, Jeum-Jong; Chung, Hyun A; Lee, Woo Song; Kim, Sung-Kyu; Yoon, Yong-Jin; Journal of Heterocyclic Chemistry; vol. 39; nb. 1; (2002); p. 203 - 212 View in Reaxys

NH 2

O O S Cl

HN

S O

Rx-ID: 630266 View in Reaxys 13/22 Yield Conditions & References With alkali Marckwald; v.Droste-Huelshoff; Chemische Berichte; vol. 32; (1899); p. 562 View in Reaxys Remsen; Palmer; American Chemical Journal; vol. 8; (1886); p. 242 View in Reaxys With indole-3-carboxaldehyde-polystyrene resin, sodium cyanoborohydride, trifluoroacetic acid, tetramethylammonium triacetoxyborohydride, Yield given. Multistep reaction Estep, Kimberly G.; Neipp, Christopher E.; Stramiello, Linda M. Stephens; Adam, Mavis D.; Allen, Martin P.; et al.; Journal of Organic Chemistry; vol. 63; nb. 16; (1998); p. 5300 - 5301

Copyright 2013 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys and the Reaxys trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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View in Reaxys in dichloromethane, Substitution Brewer, Stuart A.; Burnell, Helen T.; Holden, Ian; Jones, Brian G.; Willis, Colin R.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 6; (1999); p. 1231 - 1234 View in Reaxys

O O S Cl

2.4-dioxy-6-methoxy-benzophe none
HN

S O

Rx-ID: 15013151 View in Reaxys 14/22 Yield Conditions & References Reaction Steps: 2 1: 88 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 2.5 h / 20 C 2: 35 percent / tetrahydrofuran / 4 h / 20 - 22 C With 4-(N,N-dimethlyamino)pyridine in tetrahydrofuran Kweon, Deok-Heon; Kim, Ho-Kyun; Kim, Jeum-Jong; Chung, Hyun A; Lee, Woo Song; Kim, Sung-Kyu; Yoon, Yong-Jin; Journal of Heterocyclic Chemistry; vol. 39; nb. 1; (2002); p. 203 - 212 View in Reaxys

O H 2N S O

ethyl sulfate of sodium

HN S O O

Rx-ID: 7585346 View in Reaxys 15/22 Yield Conditions & References With sodium carbonate, T= 180 - 200 C Patent; Bayer and Co.; DE346810; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 13; p. 1103 View in Reaxys

O S N H

O Cl
Sn

HN

S O

Rx-ID: 2082252 View in Reaxys 16/22 Yield 87 % Conditions & References 1) rt, 30 min, 2) 70 deg C, 17 h Neumann, Wilhelm P.; Wicenec, Christian; Chemische Berichte; vol. 126; nb. 3; (1993); p. 763 - 768 View in Reaxys

S S N S

O O

HS

HN

S O

Rx-ID: 9996740 View in Reaxys 17/22 Yield Conditions & References With sodium hydroxide, potassium chloride, dihydrogen peroxide in 1,4-dioxane, water, T= 25 C , pH= 12, Kinetics

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Norberto, Fatima; Araujo, M. Eduarda M.; Santos, Lidia; Jaime, Marta S. P.; Mateus, Pedro M. V.; Herves, Pablo; European Journal of Organic Chemistry; nb. 21; (2005); p. 4710 - 4714 View in Reaxys With potassium chloride in 1,4-dioxane, water, T= 25 C , Kinetics Norberto, Fatima; Araujo, M. Eduarda M.; Santos, Lidia; Jaime, Marta S. P.; Mateus, Pedro M. V.; Herves, Pablo; European Journal of Organic Chemistry; nb. 21; (2005); p. 4710 - 4714 View in Reaxys

NH O O S

Tl+

S O

O (v0)

Rx-ID: 1109545 View in Reaxys 18/22 Yield Conditions & References With thallium ethylate Fletcher; Pan; Synthesis; vol. No. 1; (1975); p. 39 - 40 View in Reaxys

O O S N N+ Cl

HO NH 2

HN

S O

Rx-ID: 2859065 View in Reaxys 19/22 Yield Conditions & References in ethanol, water Monjoint, Pierre; Ruasse, Marie-Francoise; Tetrahedron Letters; vol. 25; nb. 30; (1984); p. 3183 - 3186 View in Reaxys

O H 2N S O

O O O S

HN

S O

Rx-ID: 624679 View in Reaxys 20/22 Yield Conditions & References With sodium carbonate Klammann et al.; Monatshefte fuer Chemie; vol. 83; (1952); p. 870,872,876 View in Reaxys

O H 2N S O

HN

S O

Rx-ID: 2740112 View in Reaxys 21/22 Yield Conditions & References With sodium tetrahydroborate, Hg(NO3)2, N-butylamine, 1.) methylene dichloride, reflux, 8 h, 2.) aq. sodium hydroxide, Yield given. Multistep reaction

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Barluenga, Jose; Jimenez, Carmen; Najera, Carmen; Yus, Miguel; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1984); p. 721 - 725 View in Reaxys

HN

S O

Rx-ID: 7585345 View in Reaxys 22/22 Yield 80% Conditions & References Example Name 21.B Example Title EXAMPLE 21 B. Using the procedure of Example 17A, the resin-bound N-ethylamine was converted to N-ethyl4-methylbenzenesulfonamide in 80percent yield. Patent; PFIZER INC.; EP801083; (1997); (A2) English View in Reaxys Kay,I.T.; Snell,B.K.; Tetrahedron Letters; (1967); p. 2251 - 2253 View in Reaxys Johnson,C.R. et al.; Tetrahedron Letters; (1968); p. 3719 - 3722 View in Reaxys Levcenko et al.; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 1273,1234 View in Reaxys Example Name B Example Title Preparation of 4-N-ethyl formyl phenylsulfonamide EXAMPLE B Preparation of 4-N-ethyl formyl phenylsulfonamide A suspension of 26 g of paratoluene sulfochloride in 200 cm3 of water is cooled to 0 C. With stirring there are slowly added 100 cm3 of a 40percent aqueous solution of ethylamine in water. At the end of the addition the reaction mixture is again stirred for two hours at 0 C., then for two hours at ambient temperature. The solid in suspension is filtered, washed several times with water, then dried under reduced pressure. 24 g of Nethyl(4-methyl phenyl) sulfonamide are obtained. Patent; Societe Anonyme dite: L'Oreal; US4980509; (1990); (A1) English View in Reaxys

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