Formamide → 4,5-Diphenyloxazole

HRID 868919Notes

Reaction equation

HRID 868919 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]([NH2:19])=O.OS(O)(=O)=O>C1(C)C(C)=CC=CC=1>[C:1]1([C:7]2[N:19]=[CH:17][O:10][C:9]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 1118Sulfuric AcidHCID 8400Benzoin

Product 1

HCID 6134984,5-Diphenyloxazole

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of benzoin (2.65 g, 12.5 mmol), formamide (10 mL), xylene (40 mL) and conc. H2SO4 (1 mL) was refluxed for 14 h with a dean-stark trap attached to remove water. After cooling to room temperature, water was added to the mixture. The organic layer was separated, washed, dried (with MgSO4), and then distilled under reduced pressure to give 4,5-diphenyloxazole (1.93 g) as a yellow solid.

Workup

  1. temperaturewas refluxed for 14 h with a dean-stark trap
  2. customto remove water
  3. additionwater was added to the mixture
  4. customThe organic layer was separated
  5. washwashed
  6. dry with materialdried (with MgSO4)
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-4a10fad4c4cf484ab493e8694ce890a8
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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