Dimethylformamide → 4-{[(Methylsulfanyl)methyl]sulfanyl}-2-nitroaniline

HRID 1679458Notes

Reaction equation

HRID 1679458 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+].[CH3:21][S:22]CCl>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][S:22][CH3:21])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 16916Chloromethyl methyl sulfideHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 203628244-{[(Methylsulfanyl)methyl]sulfanyl}-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.85 G. 1-amino-2-nitro-4-thiocyanatobenzene is treated in 20 ml. dimethylformamide under nitrogen at 20°-25° C. with 1.14 g. sodium borohydride. After 1 hour 10 ml. of methylthiomethylchloride is added and the mixture stirred overnight, diluted with water and extracted with chloroform. The dried chloroform solution is passed through a silica gel column, then evaporated to dryness leaving 1-amino-2-nitro-4-methylthiomethylthiobenzene as a red solid.

Workup

  1. customat 20°-25° C.
  2. extractionextracted with chloroform
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-8a65d86fadb843dca434360ffc153b1f
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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