Acetamide → 3-(2-Methyl-5-propyl-oxazol-4-yl)-benzoic acid methyl ester

HRID 1265618Notes

Reaction equation

HRID 1265618 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH:11](Br)[CH2:12][CH2:13][CH3:14])[CH:5]=1.[C:18]([NH2:21])(=[O:20])[CH3:19]>>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:21]=[C:18]([CH3:19])[O:20][C:11]=2[CH2:12][CH2:13][CH3:14])[CH:5]=1

Participants

3

Reactant 2

HCID 178AcetamideHCID 87951238Rac-3-(2-bromo-pentanoyl)-benzoic acid methyl ester

Product 1

HCID 696875703-(2-Methyl-5-propyl-oxazol-4-yl)-benzoic acid methyl esterYield 36.1%

Procedure

A sample of rac-3-(2-bromo-pentanoyl)-benzoic acid methyl ester (1.50 g) and acetamide (0.89 g) were heated together to 130° C. for 15 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 (1:3) as eluent to give 3-(2-methyl-5-propyl-oxazol-4-yl)-benzoic acid methyl ester (0.47 g) as a light-yellow oil.

Workup

  1. customThe mixture was partitioned between AcOEt and brine
  2. customthe organic layer was dried
  3. customevaporated
  4. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-4021154358aa4bf9944f0524e9181deb
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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