Methanol → 2-((7-Chloro-5-(2-chlorophenyl)-3H-1,4-benzodiazepin-2-yl)thio)-N,N-dimethylethanamine

HRID 839282Notes

Reaction equation

HRID 839282 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-].[Na+].CO.Cl.[CH3:26][N:27]([CH2:29][CH2:30]Cl)[CH3:28]>O>[CH3:26][N:27]([CH3:28])[CH2:29][CH2:30][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

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 8267037-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thioneHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 3419102-((7-Chloro-5-(2-chlorophenyl)-3H-1,4-benzodiazepin-2-yl)thio)-N,N-dimethylethanamineYield 88.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.5 g of 1,3-dihydro-5-(2-chlorophenyl)-7-chloro-2H-1,4-benzodiazepine-2-thione in a solvent mixture comprising 10 ml of a 10% aqueous sodium hydroxide solution and 10 ml of methanol is added dropwise under ice cooling with stirring an aqueous solution of 1.7 g of N,N-dimethyl-2-chloroethylamine hydrochloride, and the resulting mixture is stirred at room temperature for 2.5 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is rinsed with a 5% aqueous sodium hydroxide solution, washed with water and then dried over magnesium sulfate. The solvent is distilled off from the solution to obtain as the residue 2.7 g of an oily 2-(2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine. The oily product thus obtained is treated, according to usual procedure, with maleic acid and recrystallized from an isopropyl alcohol-acetone mixture to obtain 2.6 g of 2-(2-dimethylaminoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine maleate, m.p. 140°-142° C.

Workup

  1. additionis added dropwise under ice cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract is rinsed with a 5% aqueous sodium hydroxide solution
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off from the solution

Sources & evidence

ORD record
ord-7d8030b305fd4921b6bbb2901fe8ca6f
Source dataset
uspto-grants-1978_06
Patent number
US04094870

Reaction notes

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