Methanol → 4-(Phenylthio)benzene-1,2-diamine

HRID 1414793Notes

Reaction equation

HRID 1414793 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.CO.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O>[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

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 1707372-Nitro-5-phenylthioaniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.5 Kg. of 1-amino-2-nitro-5-phenylthiobenzene in 60 l. of methanol and 30 l. of water is treated, under nitrogen, with 8.0 kg. of sodium dithionite and 2.0 kg. of sodium carbonate at reflux. The mixture is heated for 2 hours and the methanol is removed by distillation. The mixture is cooled and extracted with dichloromethane. The dichloromethane solution is filtered, dried over sodium sulfate, and 1,2-diamino-4-phenylthiobenzene is isolated by evaporation.

Workup

  1. temperatureThe mixture is heated for 2 hours
  2. customthe methanol is removed by distillation
  3. temperatureThe mixture is cooled
  4. extractionextracted with dichloromethane
  5. filtrationThe dichloromethane solution is filtered
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-a0f0aa37979f4f9a802ad2f86e21556e
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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