反応式
[N:1]([O-])=O.[Na+].[CH3:5][C:6]1[C:10]([CH2:11][N:12]2[CH:16]=[C:15]([C:17]([NH:19][NH2:20])=[O:18])[CH:14]=[N:13]2)=[C:9]([CH3:21])[O:8][N:7]=1>C(O)(=O)C>[CH3:5][C:6]1[C:10]([CH2:11][N:12]2[CH:16]=[C:15]([C:17]([N:19]=[N+:20]=[N-:1])=[O:18])[CH:14]=[N:13]2)=[C:9]([CH3:21])[O:8][N:7]=1参加物
反応条件
- 温度
- 0 °C
実験手順
Sodium nitrite (450 mg, 6.5 mmol, in H2O) (10 mL) was added dropwise, over 10 minutes, to a suspension of 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carbohydrazide (example 10-1b) (1 g, 4.3 mmol) in 10% aqueous acetic acid (50 mL) and cooled to 0° C. via an ice water bath. The reaction was stirred for an additional 15 minutes then extracted with ethyl acetate (3×, 75 mL). The combined organic extracts were washed with aqueous saturated sodium carbonate (100 mL) followed by H2O (100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The solid product was triturated with ethyl acetate/hexanes (1/9) and dried en vacuo to afford 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carbonyl azide (1 g, 93%) as a white solid. 1H NMR (CDCl3, 400 MHz): δ2.20 (s, 3H), 2.44 (s, 3H), 5.07 (s, 2H), 7.81 (s, 1H), 7.93 (s, 1H).
後処理
- extractionthen extracted with ethyl acetate (3×, 75 mL)
- washThe combined organic extracts were washed with aqueous saturated sodium carbonate (100 mL)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe solid product was triturated with ethyl acetate/hexanes (1/9)
- customdried en vacuo
出典と根拠
- ORDレコード
- ord-0de395f19dd0489097335e19b818a320
- 出典データセット
- uspto-grants-2013_05
- 特許番号
- US08445692B2
関連ノート
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