8-chloro-6-(2-chlorophenyl)-2-methyl-4H-imidazo[1,2-a][1,4]benzodiazepine-1-carboxaldehyde → 1H-1,4-Benzodiazepine

HRID 1580652Notes

Reaction equation

HRID 1580652 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:11]3C(C=O)=C(C)N=[C:10]3[CH2:9][N:8]=[C:7](C3C=CC=CC=3Cl)[C:6]=2[CH:25]=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C1C=CC=CC=1>[NH:11]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:25][C:6]=2[CH:7]=[N:8][CH:9]=[CH:10]1

Participants

4

Reactant 1

HCID 215625108-chloro-6-(2-chlorophenyl)-2-methyl-4H-imidazo[1,2-a][1,4]benzodiazepine-1-carboxaldehyde

Product 1

HCID 1484311H-1,4-Benzodiazepine

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 241BenzeneSolvent

Procedure

A mixture of 1.0 g. of 8-chloro-6-phenyl-2,4-dimethyl-4H-imidazo[1,2-a][1,4]benzodiazepine-1-carboxaldehyde (II) and 0.1 g. of tris(triphenylphosphine)rhodium chloride in 50 ml. of benzene is refluxed for about 6 hours. The mixture is then allowed to cool and filtered to remove the catalyst. The filtrate thus obtained is concentrated in vacuo to give 8-chloro-6-phenyl-2,4-dimethyl-4H-imidazo[1,2-a][1,4-benzodiazepine, which is further purified by chromatography and/or crystallization.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureto cool
  3. filtrationfiltered
  4. customto remove the catalyst
  5. customThe filtrate thus obtained
  6. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-214243746d064b4180ff86e78f8bbc09
Source dataset
uspto-grants-1976_01
Patent number
US03933794

Reaction notes

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