Hydrochloric Acid → 4-[(Prop-2-yn-1-yl)sulfanyl]benzene-1,2-diamine

HRID 1679440Notes

Reaction equation

HRID 1679440 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=1[N+:12]([O-])=O.Cl.C(=O)(O)[O-].[K+]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=1[NH2:12]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516893Potassium BicarbonateHCID 203628142-Nitro-4-[(prop-2-yn-1-yl)sulfanyl]aniline

Product 1

HCID 203628414-[(Prop-2-yn-1-yl)sulfanyl]benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4.8 G. of 1-amino-2-nitro-4-(prop-2-yn-1-ylthio)benzene in 14 ml. concentrated hydrochloric acid is treated with a solution of 24 g. stannous chloride in 14 ml. concentrated hydrochloric acid at 20°-30° C. After about 30 minutes, the mixture is neutralized with a saturated solution of potassium bicarbonate and chloroform added. The mixture is filtered, the chloroform layer separated, dried and evaporated yielding 1,2-diamino-4-(prop-2-yn-1-ylthio)benzene.

Workup

  1. customat 20°-30° C
  2. additionadded
  3. filtrationThe mixture is filtered
  4. customthe chloroform layer separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ac2fb10819644fbabb3a3bd03a1beedf
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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