Potassium Hydroxide → 57616-48-5

HRID 839283Notes

Reaction equation

HRID 839283 reaction equation
[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

Participants

7

Reactant 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

Product 1

HCID 538503557616-48-5

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8118ee8914504e0fa9671c532a5dada5
Source dataset
uspto-grants-1978_06
Patent number
US04094870

Reaction notes

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