Carbon tetrabromide → HCID 19851581, compound

HRID 1606997Notes

Reaction equation

HRID 1606997 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH:16]=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:39][C:40](Br)(Br)[Br:41]>C(Cl)Cl>[BrH:39].[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH:16]=[C:40]([Br:41])[Br:39])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 198515847-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

Product 1

HCID 19851581HCID 19851581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.0 g (10.9 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde and 5.7 g (21.7 mmol) of triphenylphosphine were dissolved in 80 ml of methylene chloride at room temperature. Thereafter, the mixture was cooled with an ice-bath to 0° and at this temperature there was added dropwise thereto a solution of 4.0 g (12.0 mmol) of tetrabromomethane in 15 ml of methylene chloride. Thereafter, the mixture was stirred at room temperature for a further 6 hours and subsequently evaporated in a vacuum. The residue was suspended in ethyl acetate and heated under reflux for 30 minutes, cooled to 10° while stirring, suction filtered and dried. The crystalline crude product was recrystallized from alcohol and there was obtained 7-chloro-3-(2,2-dibromovinyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrobromide as white crystals of melting point 215°-217°.

Workup

  1. temperatureThereafter, the mixture was cooled with an ice-bath to 0° and at this temperature there
  2. additionwas added dropwise
  3. customsubsequently evaporated in a vacuum
  4. temperatureheated
  5. temperatureunder reflux for 30 minutes
  6. temperaturecooled to 10°
  7. stirringwhile stirring
  8. filtrationsuction filtered
  9. customdried
  10. customThe crystalline crude product was recrystallized from alcohol

Sources & evidence

ORD record
ord-3ccfc75f1c5f4c8f84166765418457e3
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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