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4,5-Dihydrodiazepam → HCID 21414257, compound

HRID 442329
Notes
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Reaction equation

HRID 442329 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:5][CH2:4][C:3]1=[O:20].[O-2].[Mg+2].[CH3:23][N:24]1[C:30]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:29]=2[CH:28]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:27]([C:42](Cl)=[O:43])[CH2:26][C:25]1=[O:45]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]([C:42]([N:27]2[CH:28]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[N:24]([CH3:23])[C:25](=[O:45])[CH2:26]2)=[O:43])[CH2:4][C:3]1=[O:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 30819844,5-DihydrodiazepamHCID 6850729Magnesium monoxideHCID 20486168HCID 20486168, compound

Product 1

HCID 21414257HCID 21414257, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1 g. of 1-methyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one and 1 g. of magnesium oxide are added to a solution of 0.8 g. (2.29 mmoles) of 1-methyl-4-chlorocarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 10 ml. of chloroform, and the mixture is stirred at 40° C. overnight. Thereafter the inorganic salts are filtered off, washed with 10 ml. of chloroform, and the chloroform solution is stirred with 10 ml. of 2n hydrochloric acid. The hydrochloride of the non-reacted base separates. The salt is filtered off, and the filtrate is washed with 5 ml. of 2.5 % aqueous sodium hydrocarbonate solution and with water. The chloroform solution is dried and evaporated. The obtained dry residue is recrystallized from ethanol. 0.91 g. (66.2 %) of di-(1-methyl-2-oxo-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-4-yl)-ketone are obtained; m.p.: 263°-266° C., Rf2 = 0.71.

Workup

  1. filtrationThereafter the inorganic salts are filtered off
  2. washwashed with 10 ml
  3. filtrationThe salt is filtered off
  4. washthe filtrate is washed with 5 ml
  5. dry with materialThe chloroform solution is dried
  6. customevaporated
  7. customThe obtained dry residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-41489eb5f57e4013b0436f20521b4b3c
Source dataset
uspto-grants-1977_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04045433

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes