Acetaldehyde → 8-Chloro-6-(2-fluorophenyl)-1-methyl-3-morpholino-4H-imidazo[1,5-a][1,4]benzodiazepine 5-oxide

HRID 128186Notes

Reaction equation

HRID 128186 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH:10]([C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:13]O)[CH2:9][N+:8]([O-:21])=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:6]=2[CH:29]=1.[CH:30](=O)[CH3:31].N>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:30]([CH3:31])=[N:13][C:12]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[C:10]3[CH2:9][N+:8]([O-:21])=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:6]=2[CH:29]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 222AmmoniaHCID 178526225HCID 178526225, compound

Product 1

HCID 130469888-Chloro-6-(2-fluorophenyl)-1-methyl-3-morpholino-4H-imidazo[1,5-a][1,4]benzodiazepine 5-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.2 g (0.01 mole) of 7-chloro-5-(2-fluorophenyl)-2,3-dihydro-N-hydroxy-α-(4-morpholinyl)-1H-1,4-benzodiazepine-2-methanimine 4-oxide, 50 ml of glacial acetic acid and 4 ml of acetaldehyde was heated to reflux for 5 minutes. The cooled reaction mixture was poured on ice, made alkaline with ammonia and extracted with methylene chloride. The extracts were dried and evaporated and the residue was crystallized from ether/2-propanol to yield yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 minutes
  3. customThe cooled reaction mixture
  4. additionwas poured on ice
  5. extractionextracted with methylene chloride
  6. customThe extracts were dried
  7. customevaporated
  8. customthe residue was crystallized from ether/2-propanol
  9. customto yield yellow crystals

Sources & evidence

ORD record
ord-b513e2526b0442d5ae6d866ccf1a83f4
Source dataset
uspto-grants-1981_03
Patent number
US04259241

Reaction notes

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