N-bromobutanimide → 2-Methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one

HRID 324469Notes

Reaction equation

HRID 324469 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:5]=2[N:6]=1.BrN1C(=O)CCC1=O.C(N(CC)C(C)C)(C)C>C1C=CC=CC=1>[CH3:1][C:2]1[O:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 122003742-Methyl-9,10-dihydro-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one

Product 1

HCID 220035762-Methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one (9.52 g) (J. Med. Chem., 1974, 17, 1316) and N-bromosuccinimide (7.95 g) in benzene (200 ml) was irradiated with a 500 Watt halogen lamp for 2 h. The mixture was then treated with N,N-diisopropylethylamine (15.5 ml) and set at reflux for 1 hour. The mixture was then partitioned between ethyl acetate and water. The organic phase was collected, dried (MgSO4) and solvent evaporated under reduced pressure. Purification was by recrystallisation from ethyl acetate to give a buff solid.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe mixture was then partitioned between ethyl acetate and water
  3. customThe organic phase was collected
  4. dry with materialdried (MgSO4) and solvent
  5. customevaporated under reduced pressure
  6. customPurification
  7. customwas by recrystallisation from ethyl acetate
  8. customto give a buff solid

Sources & evidence

ORD record
ord-e82e4fce3fb74cb1859b1e6181528104
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

Loading…