2-AMINO-N-METHYLBENZENESULFONAMIDE Chemical Properties

Melting point:

59-60℃

Boiling point:

352.9±44.0 °C(Predicted)

Density 

1.308

storage temp. 

2-8°C(protect from light)

pka

11?+-.0.10(Predicted)

Appearance

Light yellow to brown Solid

2-AMINO-N-METHYLBENZENESULFONAMIDE Usage And Synthesis

Description

2-Amino-N-methylbenzenesulfonamide is obtained by treating 2-nitrobenzenesulfonyl chloride with methylamine and subsequent reduction. Used as a dye component. The amides of 2-aminobenzenesulfonic acid can be treated with aldehydes or orthoformic acid esters to give 1,2,4-benzothiadiazine 1,1-dioxides or their dihydro compounds; these substances have been proposed as diuretics.

Synthesis

Step B / Intermediate C4: Synthesis of 2-amino-N-methylbenzenesulfonamide To a solution of N-methyl-2-nitrobenzenesulfonamide (26 g, 0.12 mol) in methanol (500 mL) was added 10% palladium carbon catalyst (2 g). The reaction mixture was stirred at room temperature under hydrogen atmosphere for 3 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford the target product 2-amino-N-methylbenzenesulfonamide (22 g, 98% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.45-7.48 (dd, 1H, J=1.6 Hz, 8.0 Hz), 7.24-7.31 (m, 2H), 6.81-6.83 (dd, 1H, J=0.6 Hz, 8.0 Hz), 6.60-6.65 (m, 1H), 5.89 (s 2H), 2.370-2.374 (d, 3H, J=1.6Hz).

References

[1] Patent: WO2012/92880, 2012, A1. Location in patent: Page/Page column 64
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 29, p. 4955 - 4957
[3] Patent: WO2007/45868, 2007, A1. Location in patent: Page/Page column 47
[4] Farmaco, Edizione Scientifica, 1954, vol. 9, p. 661,678, 680
[5] Farmaco, Edizione Scientifica, 1957, vol. 12, p. 495,499, 500

2-AMINO-N-METHYLBENZENESULFONAMIDE(16288-77-0)Related Product Information

• Chlorothiazide
• CYCLOTHIAZIDE
• DIAZOXIDE
• Althiazide
• HYDROFLUMETHIAZIDE
• Hydrochlorothiazide
• 2-Amino-N-ethylbenzenesulfonanilide
• POLYTHIAZIDE (200 MG)
• Trichlormethiazide
• BENDROFLUMETHIAZIDE
• BENZTHIAZIDE
• 7-(DIMETHYLAMINOSULPHONYL)-2,3-DIHYDRO-1-[[N-(2-METHOXYPHENYL)AMINO]CARBONYL]-(1H)-INDOLE
• (2-INDOL-3-YLETHYL)((2-NITROPHENYL)SULFONYL)AMINE
• 1-((4-(3-CHLORO-5-(TRIFLUOROMETHYL)(2-PYRIDYL))PIPERAZINYL)SULFONYL)-2-NITROBENZENE
• 2-NITRO-1-((4-(5-(TRIFLUOROMETHYL)(2-PYRIDYL))PIPERAZINYL)SULFONYL)BENZENE
• 2,3-DIHYDRO-N,N-DIMETHYL-7-(1H)-INDOLESULPHONAMIDE
• 2-AMINO-N-QUINOLIN-8-YL-BENZENESULFONAMIDE
• 1-[(ETHYLAMINO)CARBONYL]-7-(DIMETHYLAMINOSULPHONYL)-2,3-DIHYDRO-(1H)-INDOLE