Dimethylformamide → N-{2-Nitro-4-[(1,3-thiazol-2-yl)sulfanyl]phenyl}acetamide

HRID 1415520Notes

Reaction equation

HRID 1415520 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]#[N:13])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2].CN(C)C=O.[BH4-].[Na+].BrC1[S:26][CH:27]=[CH:28]N=1>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[S:26][CH:27]=[CH:28][N:13]=2)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 764302-BromothiazoleHCID 4311764Sodium borohydrideHCID 8180927Thiocyanic acid, 4-(acetylamino)-3-nitrophenyl ester

Product 1

HCID 21482791N-{2-Nitro-4-[(1,3-thiazol-2-yl)sulfanyl]phenyl}acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.37 g. of 1-acetamido-2-nitro-4-thiocyanatobenzene in 10 ml. dimethylformamide, there is added under nitrogen at less than 30° C., 0.38 g. of sodium borohydride. The mixture is stirred at 20°-30° C. for 1 hour, then 3.2 ml. of 2-bromothiazole is added. The mixture is heated to 130°-135° C. for 1 hour, then cooled and diluted with water. The crude product is filtered off and recrystallized from methanol yielding 1-acetamido-2-nitro-4-(thiazol-2-ylthio)benzene.

Workup

  1. temperatureThe mixture is heated to 130°-135° C. for 1 hour
  2. temperaturecooled
  3. filtrationThe crude product is filtered off
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-69be1e57efb341669dc6bbdf412d4473
Source dataset
uspto-grants-1977_01
Patent number
US04005202

Reaction notes

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