Dimethylformamide → N-{2-Nitro-4-[(pyrazin-2-yl)sulfanyl]phenyl}acetamide

HRID 1415524Notes

Reaction equation

HRID 1415524 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+].Cl[C:25]1[CH:30]=NC=[CH:27][N:26]=1>O.CC(C)=O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:27]=[N:26][CH:25]=[CH:30][N:13]=2)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 73277ChloropyrazineHCID 4311764Sodium borohydrideHCID 8180927Thiocyanic acid, 4-(acetylamino)-3-nitrophenyl ester

Product 1

HCID 21482788N-{2-Nitro-4-[(pyrazin-2-yl)sulfanyl]phenyl}acetamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 9.6 g. 1-acetamido-2-nitro-4-thiocyanatobenzene in 60 ml. dimethylformamide is treated under nitrogen with 1.52 g. of sodium borohydride, the exothermic reaction being controlled so that the temperature does not exceed 30° C. After stirring the mixture at 20°-25° C. for 1 hour, 15 ml. of acetone is added, then, after 2 hours, 9.1 g. of 2-chloropyrazine is added. The mixture is warmed slowly and kept at 100°-110° C. for 3 hours, cooled and diluted with water. The product is filtered off and washed with water, pentane and recrystallized from methanol affording 1-acetamido-2-nitro-4-(pyrazin-2-ylthio)benzene.

Workup

  1. customdoes not exceed 30° C
  2. waitafter 2 hours
  3. temperatureThe mixture is warmed slowly
  4. waitkept at 100°-110° C. for 3 hours
  5. temperaturecooled
  6. filtrationThe product is filtered off
  7. washwashed with water, pentane
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8d836d561434460992205b84caf87119
Source dataset
uspto-grants-1977_01
Patent number
US04005202

Reaction notes

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