Sodium Hydroxide → 4-[(4-Methylphenyl)sulfanyl]benzene-1,2-diamine

HRID 1658585Notes

Reaction equation

HRID 1658585 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]=1[N+:19]([O-])=O)(=O)C.[OH-].[Na+]>CO>[NH2:19][C:6]1[CH:7]=[CH:8][C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:10][C:5]=1[NH2:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68145278HCID 68145278, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.5 G. of 2-acetamido-4-(p-methylthiophenoxy)-1-nitrobenzene is treated on the steam bath with 7 ml. 5N sodium hydroxide and 50 ml. methanol for 1 hour. The mixture is concentrated, diluted with water and the 2-amino-4-(p-methylthiophenoxy)-1-nitrobenzene filtered off. This material is treated in 18 ml. concentrated hydrochloric acid with 18 g. stannous chloride on the steam bath for 5 minutes. The mixture is cooled, decanted and the solid washed with 18 ml. 6N hydrochloric acid. The free base is liberated by treatment with potassium bicarbonate and extracted into chloroform. Evaporation of the chloroform leaves crystalline 1,2-diamino-4-(p-methylthiophenoxy)-benzene.

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with water
  3. filtrationthe 2-amino-4-(p-methylthiophenoxy)-1-nitrobenzene filtered off
  4. additionThis material is treated in 18 ml
  5. temperatureThe mixture is cooled
  6. customdecanted
  7. washthe solid washed with 18 ml
  8. extractionextracted into chloroform
  9. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-5ef2e68377ed4adeb4788783ff76eea2
Source dataset
uspto-grants-1976_06
Patent number
US03965113

Reaction notes

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