N-bromobutanimide → 7-Bromo-4-methoxy-2-methylsulfanylbenzooxazole

HRID 2186445

Reaction equation

HRID 2186445 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[C:16]2[N:17]=[C:18]([S:20][CH3:21])[O:19][C:15]=2[CH:14]=[CH:13][CH:12]=1>C(#N)C>[Br:1][C:14]1[C:15]2[O:19][C:18]([S:20][CH3:21])=[N:17][C:16]=2[C:11]([O:10][CH3:9])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 224566644-Methoxy-2-(methylthio)benzo[d]oxazole

Product 1

HCID 224566517-Bromo-4-methoxy-2-methylsulfanylbenzooxazoleYield 33.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimide (2.4 g) was added to a solution of 4-methoxy-2-methylsulfanylbenzooxazole (2.63 g) in acetonitrile (80 ml) and the mixture stirred for 18 hours. It was then partitioned between dichloromethane (200 ml) and water (200 ml). The organics were washed with water (200 ml), dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 10% ethyl acetate in heptane afforded the title compound as a white solid (1.25 g).

Workup

  1. customIt was then partitioned between dichloromethane (200 ml) and water (200 ml)
  2. washThe organics were washed with water (200 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customPurification by column chromatography on silica eluting with 10% ethyl acetate in heptane

Sources & evidence

ORD record
ord-721a3691b2b743c5ae80a1caaa429e33
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Linked notes

Loading…