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

HRID 1679449Notes

Reaction equation

HRID 1679449 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)[O-].[K+]>C(O)(=O)C>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.35 G. of 2-amino-4-(p-methylphenylthio)-1-nitrobenzene in 16 ml. concentrated hydrochloric acid and 16 ml. acetic acid is treated with 16 g. stannous chloride on the steam bath for 1 hour. The mixture is cooled, treated with an excess of potassium bicarbonate and extracted with chloroform. Evaporation of the chloroform leaves 1,2-diamino-4-(p-methylphenylthio)benzene.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with chloroform
  3. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-2bc74785476741c09b5c51fed83fbd93
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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