4-Chloro-2-nitroaniline → 2-Nitro-5-phenylthioaniline

HRID 1679473Notes

Reaction equation

HRID 1679473 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[C:18]1([SH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([S:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 69794-Chloro-2-nitroanilineHCID 7969ThiophenolHCID 11430Potassium Carbonate

Product 1

HCID 1707372-Nitro-5-phenylthioaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.0 kg. of 1-amino-2-nitro-4-chlorobenzene and 7.2 kg. of potassium carbonate in 25 l. of DMF under nitrogen is treated with 4.0 kg. of thiophenol. The mixture is stirred for 2 hours, cooled, and diluted with 140 l. of ice water. The mixture is stirred for 1 hour, and 1-amino-2-nitro-5-phenylthiobenzene is isolated by filtration.

Workup

  1. additionA mixture of 6.0 kg
  2. temperaturecooled
  3. additiondiluted with 140 l
  4. stirringThe mixture is stirred for 1 hour

Sources & evidence

ORD record
ord-f9866c38d22d46718c7301f4138ba532
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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