Formamide → Methyl 3-[5-methyl-oxazol-4-yl]-benzoate

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH:11](Br)[CH3:12])[CH:5]=1.[CH:16]([NH2:18])=[O:17]>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:18]=[CH:16][O:17][C:11]=2[CH3:12])[CH:5]=1

Participants

Reactant 2

HCID 713Formamide

HCID 22139798Rac-3-(2-bromo-propionyl)-benzoic acid methyl ester

Product 1

HCID 18548830Methyl 3-[5-methyl-oxazol-4-yl]-benzoate

Procedure

rac-3-(2-Bromo-propionyl)-benzoic acid methyl ester (5.42 g) and formamide (3.6 ml) were heated together to 130° C. for 5 h. The mixture was partitioned between AcOEt and brine, the organic layer was dried and evaporated and the residual oil was chromatographed on silica gel using AcOEt/hexane (1:4) as eluent to give 3-(5-methyl-oxazol-4-yl)-benzoic acid methyl ester (2.52 g) as white solid.

Workup

customThe mixture was partitioned between AcOEt and brine
customthe organic layer was dried
customevaporated
customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record: ord-bd11d937a89b4538a3bbfa336493f4eb
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544985B2

Reaction notes

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