Water → Ticlopidine Hydrochloride

HRID 46674

反応式

HRID 46674 の反応式
[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

参加物

5

反応物 3

HCID 962WaterHCID 16916Chloromethyl methyl sulfide2 回HCID 6454012N-((2-chlorophenyl)methyl)thiophene-3-ethylamine

生成物 1

HCID 65335Ticlopidine Hydrochloride収率 142.2%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a0fba2b7811b4cdc877702b33bdded2f
出典データセット
uspto-grants-1979_11
特許番号
US04174448

関連ノート

読み込み中…