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

HRID 839284Notes

Reaction equation

HRID 839284 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.[H-].[Na+].[CH3:23][N:24]([CH2:26][CH2:27][CH2:28]Cl)[CH3:25].O>CN(C)C=O>[CH3:23][N:24]([CH3:25])[CH2:26][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

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 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 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.4 g of 1,3-dihydro-5-(2-chlorophenyl)-7-chloro-2H-1,4-benzodiazepine-2-thione in 50 ml of anhydrous dimethylformamide is added under cooling with stirring 1,2 g of sodium hydride (50% oily suspension), and the resulting mixture is stirred at room temperature for 20 minutes. To the mixture is added dropwise 7.6 g of N,N-dimethyl-3-chloropropylamine and the mixture is stirred at room temperature for 1.5 hours. The reaction mixture is poured into iced 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. An oily product obtained as the residue is subjected to column chromatography on alumina and eluted from the column with a benzenechloroform mixture. The eluate is treated according to usual procedure 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 anhydrous ethanol and acetone to obtain 4.3 g of 2-(3-dimethylaminopropylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine fumarate, m.p. 154°- 156° C.

Workup

  1. temperatureunder cooling
  2. stirringthe mixture is stirred at room temperature for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customAn oily product obtained as the residue
  8. washeluted from the column with a benzenechloroform mixture
  9. additionThe eluate is treated

Sources & evidence

ORD record
ord-0c218104501f4a53b19c40e4be85b2b4
Source dataset
uspto-grants-1978_06
Patent number
US04094870

Reaction notes

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