Water → 2-(Benzylthio)-N,N-dimethylnicotinamide

HRID 414006ノート

反応式

HRID 414006 の反応式
CC(C)([O-])C.[K+].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][N:16]([CH3:26])[C:17]([C:19]1[C:20](Cl)=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:18].O>CN(C)C=O>[CH3:15][N:16]([CH3:26])[C:17]([C:19]1[C:20]([S:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:18]

参加物

6

反応物 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 109652142-chloro-N,N-dimethylpyridine-3-carboxamideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 110869032-(Benzylthio)-N,N-dimethylnicotinamide収率 37.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

A solution of 25.0 g (223 mmol) of potassium t-butoxide in 100 ml of dimethylformamide was cooled to 0° C. and 22 ml (186 mmol) of benzyl mercaptan added dropwise at 0° C. After addition was complete, the reaction mixture was allowed to warm to 25° C. and stirred at this temperature for 15 minutes. The reaction mixture was then re-cooled to 0° C. and 34.0 g (186 mmol) of N,N-dimethyl-2-(chloro)-3-pyridinecarboxamide added in one portion. After an exotherm to 50° C., the mixture was heated at 80° C. for 1.5 hour. The mixture was cooled, poured into 100 ml of water and extracted with ether. The combined organic extracts were washed twice with water, then brine and dried over sodium sulfate. Concentration gave 19.2 g of a viscous yellow oil. IR (Nujol) 1640 (CONMe2) cm-1.

後処理

  1. additionAfter addition
  2. temperatureThe reaction mixture was then re-cooled to 0° C.
  3. temperatureAfter an exotherm to 50° C., the mixture was heated at 80° C. for 1.5 hour
  4. temperatureThe mixture was cooled
  5. extractionextracted with ether
  6. washThe combined organic extracts were washed twice with water
  7. dry with materialbrine and dried over sodium sulfate
  8. concentrationConcentration

出典と根拠

ORDレコード
ord-e095c60610ed4391bd00b36cd56e0f65
出典データセット
uspto-grants-1988_12
特許番号
US04789393

反応ノート

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