Benzoyl Peroxide → HCID 19917448, compound

HRID 1756282Notes

Reaction equation

HRID 1756282 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.C1C(=O)N([Br:22])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC1C=CC=CC=1>[Br:22][CH2:1][C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 146167624-Benzoxazolecarboxylic acid, 2-methyl-, methyl ester

Product 1

HCID 19917448HCID 19917448, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

453 mg (2.37 mmol) of methyl 2-methylbenzoxazole-4-carboxylate (prepared by the method in J. Heterocyclic Chem. 27, 335 (1990)) are dissolved in 40 ml of chlorobenzene, 421 mg (2.37 mmol) of NBS and 20 mg of benzoyl peroxide are added, and the resulting mixture is refluxed for 2 hours. It is concentrated, and the residue is taken up in ethyl acetate, extracted by shaking with saturated NaHCO3, 10 % strength Na2SO3 and saturated NaCl solution and dried over Na2SO4. Concentration and chromatography on SiO2 with n-heptane-ethyl acetate (2:1) yields 128 mg of the title compound.

Workup

  1. temperaturethe resulting mixture is refluxed for 2 hours
  2. concentrationIt is concentrated
  3. extractionextracted
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration and chromatography on SiO2 with n-heptane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-c8ccc6e53c2541df94865f93ffb875b3
Source dataset
uspto-grants-1995_08
Patent number
US05440046

Reaction notes

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