8-chloro-1-methyl-6-phenyl-3,3a,4,6-tetrahydro-5H-imidazo[1,5-a][1,5]benzodiazepin-5-one → 8-Chloro-4,6-dihydro-1-methyl-6-phenyl-5H-imidazo[1,5-a][1,5]benzodiazepin-5-one

HRID 2163820Notes

Reaction equation

HRID 2163820 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][CH2:14][CH:10]3[CH2:9][C:8](=[O:16])[N:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][CH:14]=[C:10]3[CH2:9][C:8](=[O:16])[N:7]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:23]=1

Participants

4

Reactant 1

HCID 227495508-chloro-1-methyl-6-phenyl-3,3a,4,6-tetrahydro-5H-imidazo[1,5-a][1,5]benzodiazepin-5-one

Product 1

HCID 227495468-Chloro-4,6-dihydro-1-methyl-6-phenyl-5H-imidazo[1,5-a][1,5]benzodiazepin-5-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 7.2 g (0.022 moles) of 8-chloro-1-methyl-6-phenyl-3,3a,4,6-tetrahydro-5H-imidazo[1,5-a][1,5]benzodiazepin-5-one, 45 g of activated manganese dioxide and 1.5 l. of toluene was stirred and refluxed for 45 minutes. The manganese dioxide was filtered off and washed well with tetrahydrofuran and methylene chloride. The filtrate was evaporated and the residue was crystallized from ethyl acetate to yield end product with mp 276°-278° C.

Workup

  1. temperaturerefluxed for 45 minutes
  2. filtrationThe manganese dioxide was filtered off
  3. washwashed well with tetrahydrofuran and methylene chloride
  4. customThe filtrate was evaporated
  5. customthe residue was crystallized from ethyl acetate
  6. customto yield end product with mp 276°-278° C.

Sources & evidence

ORD record
ord-becf298499a04cc2ba757340f96ba4c3
Source dataset
uspto-grants-1979_01
Patent number
US04137229

Reaction notes

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