3-Nitro-4-phenoxy-5-sulphamyl-benzamide → 3-Amino-4-phenoxy-5-sulphamyl-benzamide

HRID 1287765Notes

Reaction equation

HRID 1287765 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:20](=[O:23])(=[O:22])[NH2:21])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([NH2:9])=[O:8])([O-])=O.[H][H]>O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:20](=[O:23])(=[O:22])[NH2:21])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([NH2:9])=[O:8]

Participants

4

Reactant 2

HCID 215060723-Nitro-4-phenoxy-5-sulphamyl-benzamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 215060743-Amino-4-phenoxy-5-sulphamyl-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 3-nitro-4-phenoxy-5-sulphamyl-benzamide (2.4 g) in water (25 ml) 1N lithium hydroxide (10 ml) was added. The resulting solution was hydrogenated at room temperature and at 1.1 atmospheres hydrogen pressure after addition of Pd-on-carbon catalyst (0.2 g catalyst containing 10% Pd). After the hydrogen uptake had become negligible, the catalyst was removed by filtration, and the filtrate was then adjusted to pH 7.5 by addition of 4N hydrochloric acid. The precipitated 3-amino-4-phenoxy-5-sulphamyl-benzamide was isolated and dried in vacuo. The compound was obtained with a melting point of 291°-292° C.

Workup

  1. additionwas added
  2. customthe catalyst was removed by filtration
  3. additionthe filtrate was then adjusted to pH 7.5 by addition of 4N hydrochloric acid

Sources & evidence

ORD record
ord-9ebbcc857bdd49c188d533c1222f2180
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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