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

HRID 1415523ノート

反応式

HRID 1415523 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b89f60b302f54a27b02ece5de9fdb9ff
出典データセット
uspto-grants-1977_01
特許番号
US04005202

反応ノート

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