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

HRID 1266770Notes

Reaction equation

HRID 1266770 reaction equation
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=O.[CH:16]([NH2:18])=[O:17]>>[CH3:15][C:2]1[O:17][CH:16]=[N:18][C:3]=1[C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

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

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 3-(2-bromo-propionyl)-benzoate (5.42 g) and formamide (3.6 ml) was heated to 130° C. for 5 h. The mixture was cooled and partitioned between H2O and AcOEt. The organic layer was dried over Na2SO4 and evaporated and the residue was purified by chromatography on silica gel (AcOEt/hexane 1:4 as eluent) to give 1.8 g methyl 3-[5-methyl-oxazol-4-yl]-benzoate as white solid.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between H2O and AcOEt
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. customthe residue was purified by chromatography on silica gel (AcOEt/hexane 1:4 as eluent)

Sources & evidence

ORD record
ord-3ee6a4623c6e4589b2e6613d5158b6fd
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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