Phenacyl bromide → 2-(3,4-Diethoxyphenyl)-4-phenyloxazole

HRID 447906

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH3:25])[C:17]([NH2:19])=[O:18])[CH3:12].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([C:17]2[O:18][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:19]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH3:25])[CH3:12]

Participants

Conditions

Temperature: 170 °C

Procedure

In a microwave vial were dissolved 2-bromo-1-phenylethanone (95 mg, 0.478 mmol) and 3,4-diethoxybenzamide (100 mg, 0.478 mmol) in DMF (5 ml) and the reaction was heated at 170° C. for 40 min. The reaction mixture was poured in a saturated solution of NaHCO3 and extracted with EtOAc (50 ml×3). The combined organic phases were washed with a saturated solution of NaCl (30 ml×2) and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (95:5) to yield 25 mg (17%) of the product. MS (EI) m/z: 310 (M+)

Workup

extractionextracted with EtOAc (50 ml×3)
washThe combined organic phases were washed with a saturated solution of NaCl (30 ml×2)
concentrationconcentrated under reduced pressure
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-57c2cb8b99284cf88173f62fa4d99a8c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481573B2

Linked notes

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