Sodium hydride → N-{2-Nitro-4-[(pyridin-4-yl)sulfanyl]phenyl}acetamide

HRID 1580958Notes

Reaction equation

HRID 1580958 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].[BH4-].[Na+].[H-].[Na+].Cl.BrC1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>O.CC(C)=O.CN(C)C=O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 881004-Bromopyridinium chlorideHCID 4311764Sodium borohydrideHCID 8180927Thiocyanic acid, 4-(acetylamino)-3-nitrophenyl ester

Product 1

HCID 21482768N-{2-Nitro-4-[(pyridin-4-yl)sulfanyl]phenyl}acetamide

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 9.6 g. of 1-acetamido-2-nitro-4-thiocyanatobenzene in 60 ml. dimethylformamide is treated, under nitrogen, with 1.52 g. sodium borohydride at less than 25°C. The mixture is stirred for 1 hour at 20°-25°C., then 15 ml. of acetone is added and stirring continued for 2 hours. 2.5 G. of 57% sodium hydride in oil suspension is added at 20°-30°C., followed by 11.7 g. of 4-bromopyridine hydrochloride. The mixture is warmed slowly and kept at 120°-130°C. for several hours, then cooled and diluted with water, and extracted with chloroform. The chloroform solution is treated with charcoal, stripped and the residue recrystallized from methanol and washed with pentene affording 1-acetamido-2-nitro-4-(pyrid-4-ylthio)benzene.

Workup

  1. customat less than 25°C
  2. stirringstirring
  3. waitcontinued for 2 hours
  4. temperatureThe mixture is warmed slowly
  5. waitkept at 120°-130°C. for several hours
  6. temperaturecooled
  7. extractionextracted with chloroform
  8. additionThe chloroform solution is treated with charcoal
  9. customthe residue recrystallized from methanol
  10. washwashed with pentene

Sources & evidence

ORD record
ord-dc386d2bd64d40218c730b693255db1b
Source dataset
uspto-grants-1976_01
Patent number
US03935209

Reaction notes

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