Ammonia → 4-Amino-3-nitrobenzene-1-sulfonamide

HRID 346161

Reaction equation

HRID 346161 reaction equation
[NH3:1].Cl[C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14]>>[NH2:1][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 73244-Chloro-3-nitrobenzenesulfonamide

Product 1

HCID 27743884-Amino-3-nitrobenzene-1-sulfonamideYield 85%

Conditions

Temperature
100 °C

Procedure

A 100 ml stainless steel autoclave was charged with about 50 ml of liquid ammonia. Then 4-chloro-3-nitrobenzenesulfonamide (5.0 g, 21 mmol) was added and the bomb was heated in an oil bath at 100° C. for 3 h. Excess ammonia was allowed to evaporate, and the solid residue was successively washed with water, cold ethanol and ether to give 3.9 g (85%) of the title compound. M.p. 211.5°-213° C. (ethanol); 1H-NMR (DMSO-d6): 6.97 (d,J=9Hz, 1H, H-5), 7.12 (s, 2H, NH2), 7.57 (dd, J6-5 =9 Hz, J6-2 2Hz, H-6), 7.70 (broad s, 2H, NH2), 8.22 (d,J 2Hz, H-2).

Workup

  1. customto evaporate
  2. washthe solid residue was successively washed with water, cold ethanol and ether

Sources & evidence

ORD record
ord-69783e79fda64c808b606ab3355399e9
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Linked notes

Loading…