Reaktion #79239

Reaktionsgleichung

sodium hydroxide

sodium nitrate

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

tin (II) chloride

→

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

Ausbeute 85.0%

Lösungsmittel

hydrochloric acid

hydrogen chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition the reaction
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGstirred for 1.5 hours
4. 4
   Extraktionextracted with ethylacetate (3×50 mL)
5. 5
   EinengenThe solution was concentrated to a residue
6. 6
   workup.ADDITION1 M hydrogen chloride in ether was added until percipitation
7. 7
   FiltrationThe solution was filtered
8. 8
   Sonstigedried

Vorschrift

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.

Quelle