N-bromobutanimide → 2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-one

HRID 324450Notes

Reaction equation

HRID 324450 reaction equation
[CH2:1]([C:3]1[S:4][C:5]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[C:8](=[O:18])[C:6]=2[N:7]=1)[CH3:2].BrN1C(=O)CCC1=O>C1C=CC=CC=1>[CH2:1]([C:3]1[S:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[C:8](=[O:18])[C:6]=2[N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 220036352-Ethyl-9,10-dihydro-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-one

Product 1

HCID 220036592-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the product from step (i) (3.14 g) and N-bromosuccinimide (2.18 g) in benzene (40 ml) was irradiated with a 500 Watt halogen lamp for 2 h. The reaction mixture was partitioned between dichloromethane and water. The organic phase was further washed with water, collected, dried (MgSO4) and solvent evaporated under reduced pressure. The residue was dissolved in dichloromethane (25 ml) and triethylamine (10 ml) added. After stirring for 16 h the solvent/reagent were evaporated under reduced pressure. Purification was by chromatography eluting with 30-40% ethyl acetate in isohexane.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. washThe organic phase was further washed with water
  3. customcollected
  4. dry with materialdried (MgSO4) and solvent
  5. customevaporated under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane (25 ml)
  7. additiontriethylamine (10 ml) added
  8. customwere evaporated under reduced pressure
  9. customPurification
  10. washeluting with 30-40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-bebbb6ddf37b45e4b3355578fef7c23c
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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