Formamide → 1-(4-Methyloxazol-5-yl)ethanone
Reaction equation
Cl[CH:2]([C:6](=[O:8])[CH3:7])[C:3](=O)[CH3:4].[CH:9]([NH2:11])=[O:10].[OH-].[Na+].[Na+].[Cl-]>O.C(O)=O>[C:6]([C:2]1[O:10][CH:9]=[N:11][C:3]=1[CH3:4])(=[O:8])[CH3:7]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 3-chloro-2,4-pentanedione (26.8 g), formamide (18.0 g), and formic acid (50.0 g) was heated in a 140° C. oil bath and refluxed for 4 hours. The resulting dark mixture was poured into 100 ml of water, basified with 50% NaOH solution, and saturated with NaCl. The mixture was extracted with ethyl ether (3×100 ml). The ether solution was dried over sodium sulfate and concentrated. The residue was vacuum-distilled to yield 6.59 g of 5-acetyl-4-methyloxazole as a colorless liquid, 84° C. (15 torr). NMR: 2.51 (s, 3H), 2.52 (s, 3H), 7.85 (s, 1H).
Workup
- temperaturerefluxed for 4 hours
- extractionThe mixture was extracted with ethyl ether (3×100 ml)
- dry with materialThe ether solution was dried over sodium sulfate
- concentrationconcentrated
- distillationThe residue was vacuum-distilled
Sources & evidence
- ORD record
- ord-473946f827ad403eb4595c12bece05a2
- Source dataset
- uspto-grants-1995_11
- Patent number
- US05470862
Reaction notes
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