Tetrahydrofuran → 2-{[7-Chloro-5-(2-chlorophenyl)-3H-1,4-benzodiazepin-2-yl]sulfanyl}-N,N-dimethylpropan-1-amine

HRID 839292노트

반응식

HRID 839292 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[S:20])[CH2:10][N:9]=1.[OH-].[K+].O1CCCC1.Cl.[CH3:29][N:30]([CH2:32][CH:33](Cl)[CH3:34])[CH3:31]>[Cl-].[Na+]>[CH3:34][CH:33]([S:20][C:11]1[CH2:10][N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]=1)[CH2:32][N:30]([CH3:31])[CH3:29]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 942942-Chloropropyldimethylamine hydrochlorideHCID 8267037-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thione

생성물 1

HCID 129470472-{[7-Chloro-5-(2-chlorophenyl)-3H-1,4-benzodiazepin-2-yl]sulfanyl}-N,N-dimethylpropan-1-amine수율 64.2%

시약·촉매·용매 1

HCID 5234Sodium Chloride용매

실험 절차

To a solution of 4.8 g of 1,3-dihydro-5-(2-chlorophenyl)-7-chloro-2H-1,4-benzodiazepine-2-thione in a solvent mixture comprising 28 ml of a 10% aqueous potassium hydroxide solution and 1 ml of tetrahydrofuran is added at room temperature with stirring 3.6 g of N,N-dimethyl-2-chloropropylamine hydrochloride, and the resulting mixture is stirred at room temperature for 2 hours and 30 minutes. The mixture is diluted with a saturated aqueous sodium chloride solution and then extracted with ether. The extract is washed with water and dried, and the solvent is removed by distillation under reduced pressure. An oily product obtained as the residue is subjected to column chromatography on silica gel to obtain 3.9 g of crude 2-(1-methyl-2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine as free base. The crude product is dissolved in acetone and added with 1.1 g of fumaric acid. The solvent is removed by distillation under reduced pressure to obtain crude 2-(1-methyl-2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine fumarate. Recrystallization from a mixture of isopropyl alcohol, methyl alcohol and ether gives 4.1 g of 2-(2-dimethylamino-1-methylethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine fumarate, m.p. 178°-180° C., yield 52.5%.

후처리

  1. additionis added at room temperature
  2. extractionextracted with ether
  3. washThe extract is washed with water
  4. customdried
  5. customthe solvent is removed by distillation under reduced pressure
  6. customAn oily product obtained as the residue

출처 및 근거

ORD 기록
ord-79fbdc9539274462b95fa66cf6ddf890
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04094870

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