Sarcosine → 3,4-dihydro-4-methyl-6-bromo-2H-1,4-benzodiazepine-2,5(1H)-dione

HRID 223195Notes

Reaction equation

HRID 223195 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])O[C:8](=[O:9])[C:7]=12.[NH:14]([CH2:16]C(O)=O)[CH3:15]>>[Br:1][C:2]1[C:7]2[C:8](=[O:9])[N:14]([CH3:16])[CH2:15][C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1088SarcosineHCID 107526445-bromo-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 199051123,4-dihydro-4-methyl-6-bromo-2H-1,4-benzodiazepine-2,5(1H)-dione

Procedure

4.84 g (0.02 mol) of 6-bromoisatoic acid anhydride and 1.78 g (0.02 mol) of sarcosine are finely rubbed together and subsequently heated to 260° under a protective gas for 6 minutes. After cooling, the crude product is chromatographed on silica gel using chloroform/methanol (20:1) for the elution. After recrystallization from chloforom/hexane, there is obtained 6-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 232°-233°.

Workup

  1. temperaturesubsequently heated to 260° under a protective gas for 6 minutes
  2. temperatureAfter cooling
  3. customthe crude product is chromatographed on silica gel
  4. washfor the elution
  5. customAfter recrystallization from chloforom/hexane

Sources & evidence

ORD record
ord-0d489908d86a4758aa29ceb321b10521
Source dataset
uspto-grants-1982_10
Patent number
US04352817

Reaction notes

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