Water → Ticlopidine Hydrochloride

HRID 46674

반응식

HRID 46674 반응식
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.Cl[CH2:18]SC.O>CS(C)=O>[ClH:1].[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][C:8]2[S:9][CH:10]=[CH:11][C:12]=2[CH2:18]1

참가 물질

5

반응물 3

HCID 962WaterHCID 16916Chloromethyl methyl sulfide2회HCID 6454012N-((2-chlorophenyl)methyl)thiophene-3-ethylamine

생성물 1

HCID 65335Ticlopidine Hydrochloride수율 142.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

To 52 g (0.2 M) N-(2-chloro-benzyl)-2-(2-thienyl)ethylamine dissolved in 60 ml dimethylsulfoxide and heated at 60° C. are added, over 30 minutes, 51 g (0.3 M) crude chloromethylmethylthioether prepared in step (a) above. The temperature of the reaction medium increases gradually and it is maintained at 80°-85° C, throughout the addition step, by cooling with water. When addition of chloromethyl methylthioether is completed, the medium is cooled to 6° C. The desired product precipitates out readily. After filtration and washing with 2×70 ml acetone, there are obtained 44.1 g 5-(2-chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine hydrochloride (Yield: 73.5%). Treatment of the filtrates provides another 10 g of the desired product (Yield: 90% M.p.=190° C.). The resulting crude product contains 1-2% impurities and may be made analytically pure by recrystallization from ethanol.

후처리

  1. additionare added, over 30 minutes
  2. temperatureThe temperature of the reaction medium increases gradually
  3. temperatureit is maintained at 80°-85° C, throughout the addition step
  4. temperaturethe medium is cooled to 6° C
  5. customThe desired product precipitates out readily
  6. filtrationAfter filtration
  7. washwashing with 2×70 ml acetone, there

출처 및 근거

ORD 기록
ord-a0fba2b7811b4cdc877702b33bdded2f
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04174448

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