Dimethylformamide → N-[4-(Benzylsulfanyl)-2-nitrophenyl]acetamide

HRID 616074Notes

Reaction equation

HRID 616074 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]#N)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2].CN(C)C=O.[BH4-].[Na+].C(Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 8180927Thiocyanic acid, 4-(acetylamino)-3-nitrophenyl ester

Product 1

HCID 20362823N-[4-(Benzylsulfanyl)-2-nitrophenyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.37 G. of 1-acetamido-2-nitro-4-thiocyanatobenzene is dissolved in 10 ml. of dimethylformamide under nitrogen and 0.38 g. of sodium borohydride added at 20°-30° C. The mixture is stirred for one hour and then 2.4 ml. of benzylbromide is added. After a further 2 hours the mixture is diluted with water and the product filtered off and washed with water and hexane. Recrystallation from methanol gives pure 1-acetamido-2-nitro-4-benzylthiobenzene.

Workup

  1. filtrationthe product filtered off
  2. washwashed with water and hexane

Sources & evidence

ORD record
ord-4613ec4019af4244b338f89937cf7ef2
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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