反応 #61848

反応方程式

4-(2-methoxy-naphthalen-1-yl)-oxazol-2-ylamine

triethylamine

acetyl chloride

→

N-[4-(2-methoxy-naphthalen-1-yl)-oxazol-2-yl]-acetamide

収率 36.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他the reaction was quenched by the addition of a mixture of dichloromethane and methanol
2. 2
   洗浄The solution was washed with brine (×2)
3. 3
   乾燥dried over magnesium sulfate
4. 4
   ろ過filtered
5. 5
   その他the solvent removed under reduced pressure
6. 6
   その他The residue was purified by column chromatography
7. 7
   洗浄eluting with 2% methanol in dichloromethane

実験手順

To a solution of 4-(2-methoxy-naphthalen-1-yl)-oxazol-2-ylamine (17, 450 mg), triethylamine (0.78 mL) and dichloromethane (5 mL) at 0° C. was added acetyl chloride (0.2 mL). The solution was allowed to warm to room temperature overnight and the reaction was quenched by the addition of a mixture of dichloromethane and methanol. The solution was washed with brine (×2), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography, eluting with 2% methanol in dichloromethane, to afford N-[4-(2-methoxy-naphthalen-1-yl)-oxazol-2-yl]-acetamide (25) (190 mg, 36%) as an off-white solid. 1H NMR (DMSO-D6): 2.1 (3H, br s), 3.9 (3H, s), 7.2 (1H, s), 7.35-7.40 (1H, m), 7.45-7.50 (1H, m), 7.55 (1H, d, J=9.2 Hz), 7.90-7.95 (2H, m), 8.05 (1H, d, J=9.2 Hz), 11.2 (1H, br s). Mass Spectrum (m/z): 283 (M+H)+.

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