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

HRID 1580958노트

반응식

HRID 1580958 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dc386d2bd64d40218c730b693255db1b
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03935209

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