Ethyl Acetate → HCID 15644570, compound

HRID 728188Notes

Reaction equation

HRID 728188 reaction equation
[CH2:1]([N:3]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:9]=2[N:10]=1)[CH:4]=[O:5])[CH3:2].[Br:16]N1C(=O)CCC1=O.C(OCC)(=O)C>C1C=CC=CC=1>[Br:16][CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[N:10]=[C:6]([N:3]([CH2:1][CH3:2])[CH:4]=[O:5])[O:7][C:8]=2[CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 15171508HCID 15171508, compound

Product 1

HCID 15644570HCID 15644570, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The mixture of 2-(N-ethylformamido)-6-methylbenzoxazole (7.6 g), N-bromosuccinimide (6.6 g) and benzoyl perioxide (0.2 g) in benzene (150 ml) was refluxed for 70 minutes and the mixture was cooled to ambient temperature. To the reaction mixture was added ethyl acetate, and the mixture was washed with water and dried over magnesium sulfate. The solvent was evaporated and the residue was triturated in a mixture of diisopropyl ether and n-hexane to give 6-bromomethyl-2-(N-ethylformamido)benzoxazole (6.18 g).

Workup

  1. temperaturewas refluxed for 70 minutes
  2. washthe mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was triturated in a mixture of diisopropyl ether and n-hexane

Sources & evidence

ORD record
ord-0ad38b1b45d4435097ba5232b4b99e97
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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