ChemicalBook CAS DataBase List N-Methyl-1H-Indole-5-EthaneSulphonamide

N-Methyl-1H-Indole-5-EthaneSulphonamide synthesis

13synthesis methods

Product Name:N-Methyl-1H-Indole-5-EthaneSulphonamide
CAS Number:98623-50-8
Molecular formula:C11H14N2O2S
Molecular Weight:238.31

At 40-45 ℃ (hydrogen pressure: 3-4 kg/cm2), 2-(3-Phenylsulf-anyl-1H-indol-5-yl)-ethanesulfonic acidmethylamide (14) (5 g, 0.014 mol) was hydrogenated in ethanol: water (7:3) (40 ml) in an autoclave for 10 h. After that, the reaction mass was cooled to room temperature, followed by removing the catalyst through filtering. The filtrate was distilled out to get N-Methyl-1H-Indole-5-EthaneSulphonamide.

1H-Indole-5-ethanesulfonamide, N-methyl-3-(phenylthio)-

1204192-94-8
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98623-50-8
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Yield:98623-50-8 95%

Reaction Conditions:

with hydrogen at 40 - 45; under 2250.23 - 3000.3 Torr; for 10 h;Autoclave;

Steps:

3.4. 2-(1H-Indol-5-yl)-ethanesulfonic acidmethylamide(1)

2-(3-Phenylsulf-anyl-1H-indol-5-yl)-ethanesulfonic acidmethylamide (14) (5 g, 0.014 mol) was hydrogenated inethanol: water (7:3) (40 ml) in a autoclave at 40-45oC under3-4 kg/cm2 hydrogen pressure for 10 hrs. After completionof the reaction the reaction mass was cooled to room temperatureand was filtered to remove the catalyst. The filtratewas distilled out to get the product as a white solid whichwas re-crystallised with isopropyl alcohol to give 2-(1HIndol-5-yl)-ethanesulfonic acid methylamide (1). Yield: 3.2g (95%). Mp 260oC. Molecular formula: C11H14N2O2S; Calc.C, 55.46; H, 5.88; N, 11.76, Found: C, 55.34; H, 5.90; N,11.70; IR(KBr, νmax, cm-1): 3415(-NH str of sulfonamide),3289(-NH str of indole);1H NMR(400 MHz, δ ppm, DMSO):2.68(s, 3H,C12-H), 3.14(dd, 2H, J = 4.12 Hz, J = 5.92 Hz,C10-H), 3.27(dd, 2H, J = 4.16 Hz, J = 5.20 Hz, C11-H),6.39(t, 1H, -NH sulfonamide), 6.44(s, 1H, ArC3-H), 6.97(dd,1H, J = 1.40 Hz, J = 1.44 Hz, ArC6-H), 7.19(t, 1H, ArC2-H),7.35(d, 1H, J = 8.28 Hz, ArC7-H), 7.40(s, 1H, ArC4-H),10.34(s, 1H, -NH indole); 13C NMR (400 MHz, δ ppm,DMSO):29.12(C-12),30.00(C-10), 52.65(C-11), 101.29(C-3), 111.82(C-7), 119.72(C-6), 121.91(C-4), 125.44(C-2),128.29(C-9), 128.78(C-8), 135.12(C-5),199.17(C-4); MS(m/z): 237.00[M-1]-.

References:

Behera, Ajaya Kumar;Majumdar, Poulomi;Mohanta, Prajna Parimita;Mishra, Sushanta Kumar [Letters in Organic Chemistry,2018,vol. 15,# 4,p. 265 - 269]