Acetamide → 3-(2-Methyl-oxazol-4-yl)-benzoic acid

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])=O.[C:14]([NH2:17])(=[O:16])[CH3:15]>>[CH3:15][C:14]1[O:16][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])[N:17]=1

Participants

Reactant 2

HCID 178Acetamide

HCID 27568353-(Bromoacetyl)benzoic acid

Product 1

HCID 186131593-(2-Methyl-oxazol-4-yl)-benzoic acidYield 74.3%

Conditions

Temperature: 130 °C

Procedure

A mixture of 3-(2-bromo-acetyl)-benzoic acid (2.43 g) and acetamide (1.77 g) was heated with stirring to 130° C. for 40 min. The mixture was cooled and diluted with H2(30 mL) and the precipitate formed was collected by filtration to give 3-(2-methyl-oxazol-4-yl)-benzoic acid (1.51 g) as brown solid.

Workup

temperaturewas heated
temperatureThe mixture was cooled
additiondiluted with H2(30 mL)
customthe precipitate formed
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-1fbba387afe0432ea075cd882750885f
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544985B2

Reaction notes

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