Potassium Hydroxide → 2-(2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine maleate

HRID 839283ノート

反応式

HRID 839283 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+].Cl.[CH3:24][N:25]([CH2:27][CH2:28]Cl)[CH3:26].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34]>O.O1CCCC1>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[CH3:24][N:25]([CH3:26])[CH2:27][CH2:28][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

参加物

7

反応物 4

HCID 14797Potassium HydroxideHCID 444266Maleic AcidHCID 8267037-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thioneHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

生成物 1

HCID 53850352-(2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine maleate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3.2 g of 1,3-dihydro-5-(2-chlorophenyl)-7-chloro-2H-1,4-benzodiazepine-2-thione in a solvent mixture comprising 17 ml of a 10% aqueous potassium hydroxide solution and 1.2 ml of tetrahydrofuran is added at room temperature with stirring 2.16 g of N,N-dimethyl-2-chloroethylamine hydrochloride in its powdery form. The resulting mixture is stirred at room temperature for 3 hours and, thereafter, the reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water, dried and then distilled under reduced pressure to remove the solvent, whereby an oily 2-(2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine is obtained. The oily product thus obtained is treated, according to usual procedure, with maleic acid and recrystallized from an isopropyl alcohol-acetone mixture to obtain 4.50 g of 2-(2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine maleate, m.p. 140°-142° C.

後処理

  1. additionis added at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent, whereby an oily 2-(2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine
  7. customis obtained
  8. customThe oily product thus obtained
  9. additionis treated
  10. customrecrystallized from an isopropyl alcohol-acetone mixture

出典と根拠

ORDレコード
ord-8118ee8914504e0fa9671c532a5dada5
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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