Dimethylformamide → 2-Nitro-4-[(prop-2-yn-1-yl)sulfanyl]aniline

HRID 616092Notes

Reaction equation

HRID 616092 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]#N)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CN(C)C=O.[BH4-].[Na+].[CH2:21](Br)[C:22]#C>O.C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:21]#[CH:22])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 203628142-Nitro-4-[(prop-2-yn-1-yl)sulfanyl]aniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

5.85 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. dimethylformamide is treated, under nitrogen, with 1.14 g. sodium borohydride at 20°-30° C. After 1 1/2 hours 5 ml. of propargyl bromide is added. The mixture is stirred for three hours at 20°-30° C, then diluted with water. The product, a red solid, is isolated by extraction into chloroform yielding 1-amino-2-nitro-4-propargylthiobenzene.

Workup

  1. customat 20°-30° C
  2. customAfter 1 1/2 hours 5 ml

Sources & evidence

ORD record
ord-ca32f4ca4a7840a5b4011f314be3cec0
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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