Hydrochloric Acid → 4-(Phenylthio)benzene-1,2-diamine

HRID 1658577Notes

Reaction equation

HRID 1658577 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:15]([O-])=O.Cl.C(=O)(O)[O-].[K+]>C(Cl)(Cl)Cl>[NH2:15][C:3]1[CH:4]=[CH:5][C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1707372-Nitro-5-phenylthioanilineHCID 516893Potassium Bicarbonate

Product 1

HCID 30164174-(Phenylthio)benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.5 G. of 2-amino-4-phenylthio-1-nitrobenzene in 8 ml. conc. hydrochloric acid is treated with a solution of 16 g. of stannous chloride in 8 ml. conc. hydrochloric 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 yielding 1,2-diamino-4-phenylthiobenzene.

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-7d99f16be65748f08c629390666521ed
Source dataset
uspto-grants-1976_06
Patent number
US03965113

Reaction notes

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