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

HRID 1085247노트

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HRID 1085247 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 110869032-(Benzylthio)-N,N-dimethylnicotinamide수율 37.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1b0d6ea7a6d04824b62c3017c7206896
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05008393

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