3-nitro-N-(phenylsulfonyl)Benzamide → 3-Amino-N-(phenylsulfonyl)benzamide

HRID 1463778Notes

Reaction equation

HRID 1463778 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.[Pd]>[C:16]1([S:13]([NH:12][C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[NH2:1])=[O:11])(=[O:15])=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 9757333-nitro-N-(phenylsulfonyl)Benzamide

Product 1

HCID 184055003-Amino-N-(phenylsulfonyl)benzamideYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of the foregoing nitro compound (14.8 g, 48 mmol) in ethanol (240 ml) was hydrogenated over 10% palladium on carbon (1.4 g) at 45 psi for 1.5 hours. The reaction mixture was filtered then evaporated and the crude product recrystallised from hot ethanol to afford 3-(phenylsulphonylaminocarbonyl)aniline (10.57 g, 80%) as a colourless crystalline solid, mp 138° C. Rf=0.42 in dichloromethane/methanol (9:1) on silica plates.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthen evaporated
  3. customthe crude product recrystallised from hot ethanol

Sources & evidence

ORD record
ord-25ee280379f14799b2584db69f3aa5f3
Source dataset
uspto-grants-1994_04
Patent number
US05302591

Reaction notes

Loading…