Sodium Hydroxide → 1-{2-[(3-Chloropropyl)sulfanyl]-5-nitrophenyl}hydrazine

Temperature

0 °C

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.

1. additionAfter addition the reaction
2. temperatureto warm to room temperature
3. stirringstirred for 1.5 hours
4. extractionextracted with ethylacetate (3×50 mL)
5. concentrationThe solution was concentrated to a residue
6. addition1 M hydrogen chloride in ether was added until percipitation
7. filtrationThe solution was filtered
8. customdried

ORD record

ord-158aa48d175e48018fb2e79a9cddcf42

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE039679E1