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

HRID 1730822Notes

Reaction equation

HRID 1730822 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][CH2:23]CCl>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:21][S:22][CH3:23])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 109652-Chloroethyl methyl sulfideHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 536382734-{[2-(Methylsulfanyl)ethyl]sulfanyl}-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.85 G. of 1-amino-2-nitro-4-thiocyanatobenzene is treated in 20 ml. dimethylformamide under nitrogen at 20°-25° with 1.14 g. sodium borohydride. After 1 hour 10 ml. of methylthioethylchloride 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 to afford 1-amino-2-nitro-4-methylthioethylthiobenzene.

Workup

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

Sources & evidence

ORD record
ord-9509cb1308b84299b432ecf7f7bcbc7c
Source dataset
uspto-grants-1976_11
Patent number
US03993768

Reaction notes

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