Tetrahydrofuran → 2-(3-dimethylaminopropylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine

HRID 839285Notes

Reaction equation

HRID 839285 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+].O1CCCC1.Cl.[CH3:29][N:30]([CH2:32][CH2:33][CH2:34]Cl)[CH3:31]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:29][N:30]([CH3:31])[CH2:32][CH2:33][CH2:34][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 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 8267037-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thione

Product 1

HCID 129470492-(3-dimethylaminopropylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
40 °C

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 are added at room temperature with stirring 1.75 g of N,N-dimethyl-3-chloropropylamine hydrochloride and 100 mg of benzyltriethylammonium chloride, and the resulting mixture is stirred on a water bath at 40° C. for 4 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water and dried over magnesium sulfate and, thereafter, the solvent is distilled off under reduced pressure to obtain an oily 2-(3-dimethylaminopropylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine. The oily product thus obtained is treated, according to usual procedure, with fumaric acid and recrystallized from isopropyl alcohol to obtain 4.40 g of 2-(3-dimethylaminopropylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine fumarate, m.p. 154°-156° C.

Workup

  1. additionare added at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-c7c9f789ccc94c80b5bf117117e248d1
Source dataset
uspto-grants-1978_06
Patent number
US04094870

Reaction notes

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