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 1763251Notes

Reaction equation

HRID 1763251 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-b2280064700b4bd081c0dd38020f1f99
Source dataset
uspto-grants-1978_09
Patent number
US04111931

Reaction notes

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