Dimethylformamide → 2-Nitro-5-phenylthioaniline

HRID 616096Notes

Reaction equation

HRID 616096 reaction equation
[H-].[Na+].CN(C)C=O.[C:8]1([SH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:15][C:16]1[CH:21]=[C:20](Cl)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]>O>[NH2:15][C:16]1[CH:21]=[C:20]([S:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 1707372-Nitro-5-phenylthioaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.53 G. 57% sodium hydride in oil suspension in 20 ml. dimethylformamide is treated with 6.2 ml. thiophenol under nitrogen. 5.0 G. 2-amino-4-chloro-1-nitrobenzene is added and the mixture stirred for three hours. Water is added and the product filtered off and washed with water and hexane. Recrystallization from methanol gives pure 2-amino-4-phenylthio-1-nitrobenzene.

Workup

  1. filtrationthe product filtered off
  2. washwashed with water and hexane
  3. customRecrystallization from methanol

Sources & evidence

ORD record
ord-5a63d8bc2d7d48a58bccc89211b60f8a
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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