Carbon Dioxide → 7-Bromo-4-methyl-3,4-dihydro-1H-benzo[E][1,4]diazepine-2,5-dione

HRID 1447371Notes

Reaction equation

HRID 1447371 reaction equation
[Br:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[NH:14]([CH2:16]C(O)=O)[CH3:15].C(=O)=O>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:9])[CH2:15][N:14]([CH3:16])[C:7](=[O:8])[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 1088SarcosineHCID 2885615-Bromoisatoic Anhydride

Product 1

HCID 52976447-Bromo-4-methyl-3,4-dihydro-1H-benzo[E][1,4]diazepine-2,5-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 39.5 g of 5-bromoisatoic acid anhydride and 14.5 g of sarcosine in 150 ml of dimethyl sulphoxide is heated to 100° C. while stirring. In so doing, a vigorous evolution of carbon dioxide occurs from 70° C. and this has finished after ca 30 minutes. The mixture is stirred at 100° C. for a further 30 minutes and thereafter the mixture is poured into 900 ml of ice-water (temperature 5° C.) and the separated material is filtered off under suction. The crystals are washed with water and subsequently dried at 50° C. over phosphorus pentoxide in a vacuum drying cabinet. There is obtained 7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione in the form of light beige crystals. A sample recrystallized from methanol has a melting point of 260°-261° C.

Workup

  1. customoccurs from 70° C.
  2. waitthis has finished after ca 30 minutes
  3. stirringThe mixture is stirred at 100° C. for a further 30 minutes
  4. filtrationthe separated material is filtered off under suction
  5. washThe crystals are washed with water
  6. dry with materialsubsequently dried at 50° C. over phosphorus pentoxide in a vacuum
  7. customdrying cabinet

Sources & evidence

ORD record
ord-7951cb1bd90744c0b2b337c55007ae9e
Source dataset
uspto-grants-1982_02
Patent number
US04316839

Reaction notes

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