Ethanol → 7-Chloro-5-(2'-chloro-phenyl)-1,3-dihydro-3-(dimethylaminomethylene)-1-methyl-2H-1,4-benzodiazepin-2-one

HRID 1076388Notes

Reaction equation

HRID 1076388 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:6]=2[CH:21]=1.C(O)C>C(OC(OCC)N(C)C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9](=[CH:10][N:11]([CH3:12])[CH3:5])[N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 76168Chlorodiazepam

Product 1

HCID 536319327-Chloro-5-(2'-chloro-phenyl)-1,3-dihydro-3-(dimethylaminomethylene)-1-methyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 70913Dimethylformamide diethylacetalSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of 55 gm of 7-chloro-5-(2'-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one in 85 ml of N,N-dimethyl-formamide diethylacetal was heated to 130°C in a vessel equipped with a descending condenser, whereby a clear solution was formed after a short time. The temperature of the reaction solution was maintained at 130°C for 41 hours, during which time the ethanol formed by the reaction slowly distilled over. Thereafter, the reaction solution was cooled to about 80°C and then admixed with 50 ml of isopropanol. Upon further cooling of the mixture, a reddish-orange crystalline substance separated out which was collected by vacuum filtration, washed with petroleum ether and recrystallized from isopropanol, whereupon it had a melting point of 202°-203°C. It was identified to be the compound of the formula ##SPC5##

Workup

  1. customequipped with a descending condenser
  2. customwhereby a clear solution was formed after a short time
  3. customformed by the reaction
  4. distillationslowly distilled over
  5. temperatureThereafter, the reaction solution was cooled to about 80°C
  6. temperatureUpon further cooling of the mixture
  7. customa reddish-orange crystalline substance separated out which
  8. filtrationwas collected by vacuum filtration
  9. washwashed with petroleum ether
  10. customrecrystallized from isopropanol, whereupon it

Sources & evidence

ORD record
ord-5b2cab4e87914c96915369f9b9da10d7
Source dataset
uspto-grants-1976_05
Patent number
US03956492

Reaction notes

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