Formamide → 4-(4-Methoxyphenyl)-1,3-oxazole

HRID 2080694Notes

Reaction equation

HRID 2080694 reaction equation
[CH:1]([NH2:3])=[O:2].Br[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=O>C(OCC)(=O)C>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:3]=[CH:1][O:2][CH:5]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 4965Bromomethyl 4-methoxyphenyl ketone

Product 1

HCID 124631394-(4-Methoxyphenyl)-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

10 ml of formamide was added to 2 g of 2-bromo-4′-methoxyacetophenone, and stirred at 180° C. for 20 minutes. This was restored to room temperature, diluted with ethyl acetate, and washed with water and saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane to hexane/ethyl acetate=7/3) to obtain 0.76 g of the entitled compound.

Workup

  1. customThis was restored to room temperature
  2. washwashed with water and saturated saline water
  3. customAfter dried
  4. customthe solvent was evaporated away under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (developing solvent: hexane to hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-cb94e378d46a47e19b077ffa572d000b
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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