Acetic Acid → 4-[(4-Methylphenyl)sulfanyl]benzene-1,2-diamine

HRID 1658579Notes

Reaction equation

HRID 1658579 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:16]([O-])=O.Cl.C(O)(=O)C.C(=O)(O)[O-].[K+]>C(Cl)(Cl)Cl>[NH2:16][C:3]1[CH:4]=[CH:5][C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 516893Potassium BicarbonateHCID 203628195-[(4-Methylphenyl)sulfanyl]-2-nitroaniline

Product 1

HCID 203628214-[(4-Methylphenyl)sulfanyl]benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.5 G. of 2-amino-4-(p-methylphenylthio)-1-nitrobenzene in 8 ml. concentrated hydrochloric acid is treated with a solution of 16 g. stannous chloride in 8 ml. concentrated hydrochloric acid in 20 ml. acetic acid. The mixture is heated for 1 hour on a steam bath, cooled and treated with potassium bicarbonate and chloroform. The mixture is filtered and the chloroform layer evaporated. The residue is triturated with hot cyclohexane giving 1,2-diamino-4-(p-methylphenylthio)-benzene.

Workup

  1. temperatureThe mixture is heated for 1 hour on a steam bath
  2. temperaturecooled
  3. filtrationThe mixture is filtered
  4. customthe chloroform layer evaporated
  5. customThe residue is triturated with hot cyclohexane

Sources & evidence

ORD record
ord-ea591a5f091c49868fb674b6c87f4474
Source dataset
uspto-grants-1976_06
Patent number
US03965113

Reaction notes

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