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

HRID 839292ノート

反応式

HRID 839292 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5234Sodium Chloride溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-79fbdc9539274462b95fa66cf6ddf890
出典データセット
uspto-grants-1978_06
特許番号
US04094870

反応ノート

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