Hydrochloric Acid → 1,2-Diamino-4-n-butylthiobenzene

HRID 616110Notes

Reaction equation

HRID 616110 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][C:3]=1[N+:13]([O-])=O.Cl>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][C:3]=1[NH2:13]

Participants

3

Reactant 2

HCID 313Hydrochloric Acid2×HCID 110315614-(Butylsulfanyl)-2-nitroaniline

Product 1

HCID 203710591,2-Diamino-4-n-butylthiobenzene

Procedure

4 G. of 1-amino-2-nitro-4-n-butylthiobenzene is treated in 12 ml. concentrated hydrochloric acid with a solution of 24 g. stannous chloride in 12 ml. concentrated hydrochloric acid. The mixture is kept on the steam bath for 10 minutes, then cooled and the gummy product is washed with 12 ml. 6N hydrochloric acid. The salt is dissolved in water, treated with sodium hydroxide, and the mixture extracted with chloroform. Evaporation of the extracts followed by crystallation of the crude product from benzene yields 1,2-diamino-4-n-butylthiobenzene.

Workup

  1. temperaturecooled
  2. washthe gummy product is washed with 12 ml
  3. dissolutionThe salt is dissolved in water
  4. additiontreated with sodium hydroxide
  5. extractionthe mixture extracted with chloroform
  6. customEvaporation of the extracts

Sources & evidence

ORD record
ord-f4845dbbd1d3419182008fc4b22fab37
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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