反应 #79239

反应方程式

sodium hydroxide

sodium nitrate

2-[(3-Chloropropyl)sulfanyl]-5-nitrophenylamine

tin (II) chloride

→

1-{2-[(3-chloropropyl)sulfanyl]-5-nitrophenyl}hydrazine

收率 85.0%

溶剂

hydrochloric acid

hydrogen chloride

反应条件

后处理

1. 1
   workup.ADDITIONAfter addition the reaction
2. 2
   温度to warm to room temperature
3. 3
   workup.STIRRINGstirred for 1.5 hours
4. 4
   萃取extracted with ethylacetate (3×50 mL)
5. 5
   浓缩The solution was concentrated to a residue
6. 6
   workup.ADDITION1 M hydrogen chloride in ether was added until percipitation
7. 7
   过滤The solution was filtered
8. 8
   其他dried

实验过程

2-[(3-Chloropropyl)sulfanyl]-5-nitrophenylamine (100 mg, 0.44 mmol) was dissolved in hydrochloric acid (1.8 mL) in an ice bath, 1 M aqueous sodium nitrate (0.5 mL) was added dropwise. This was stirred at 0° C. for 1.5 hours. 0.25 M tin (II) chloride in hydrogen chloride (3.28 mL) was added dropwise. After addition the reaction was allowed to warm to room temperature, and stirred for 1.5 hours. The reaction was basified with 50% sodium hydroxide until pH of 14 and extracted with ethylacetate (3×50 mL). The solution was concentrated to a residue, taken up in minimal chloroform and 1 M hydrogen chloride in ether was added until percipitation. The solution was filtered and dried to give 1-{2-[(3-chloropropyl)sulfanyl]-5-nitrophenyl}hydrazine (100 mg, 85%). 1H NMR (CDCl3, 300 MHz): δ7.94 (d, 1H, J=2.5 Hz), 7.3 (dd, 1H, J=8.5 Hz, J=8.4 Hz ), 7.38 (d, 1H, J=8.4 Hz), 6.28 (s-broad, 1H), 3.73 (s-broad, 2H), 3.63 (t, 2H, J=6.3 Hz ), 3.00 (t, 2H, J=7 Hz), 2.01 (q, 2H, J=6.5 Hz) ppm.

来源