反应 #742297

反应方程式

2-(Ethoxymethylene)malononitrile

(2,6-Dichlorophenyl)hydrazine hydrochloride

NaOH

→

product

收率 94.5%

5-amino-1-(2,6-dichlorophenyl)-1H-pyrazole-4-carbonitrile

收率 94.5%

溶剂

EtOAc

反应条件

后处理

1. 1
   其他The organic layer separated
2. 2
   洗涤washed with water (50 mL), brine (50 mL)
3. 3
   干燥dried (MgSO4)
4. 4
   过滤filtered
5. 5
   浓缩concentrated
6. 6
   其他was suspended in methanol (50 mL) under nitrogen at −5° C
7. 7
   温度heated
8. 8
   温度at reflux under nitrogen for 2 hours
9. 9
   温度to cool
10. 10
    其他evaporated to dryness

实验过程

(2,6-Dichlorophenyl)hydrazine hydrochloride (5 g, 23.42 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL). The organic layer separated and washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated. The resultant oil was suspended in methanol (50 mL) under nitrogen at −5° C. 2-(Ethoxymethylene)malononitrile (2.86 g, 23.42 mmol) added portion-wise over 5 mins and the mixture stiffed at 0° C. for 30 mins. The reaction mixture was allowed to warm to room temperature and then heated at reflux under nitrogen for 2 hours. The reaction mixture was allowed to cool and evaporated to dryness to afford the product (5.60 g, 94%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 4.47 (2H, s), 7.43-7.47 (1H, m), 7.51-7.53 (2H, m), 7.73 (1H, s); m/z (ES+) (M+H)+=253; HPLC tR=1.62 min. Alternatively the product was obtained by concentrating the reaction mixture to half volume and allowing the product to crystallise.

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