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

HRID 1265615Notes

Reaction equation

HRID 1265615 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

3

Reactant 2

HCID 713FormamideHCID 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

  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-bd11d937a89b4538a3bbfa336493f4eb
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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