Stannous Chloride → HCID 21952754, compound

Temperature

0 °C

2-(Methylmercapto)aniline (23.6 g, 169.5 mmol) was suspended in conc. HCl (200 mL) and trifluoroacetic acid (130 mL), and cooled to 0° C. in an ice bath. Sodium nitrite (14.0 g, 203.4 mmol) was dissolved in water (45 mL) and added dropwise to the suspension over 45 minutes. After the addition, the reaction was stirred at 0° C. for 1 h. In a separate flask, tin (II) chloride (76 g, 338.4 mmol) was dissolved in conc. HCl (100 mL) and added slowly over 15 minutes to the reaction mixture. The resultant suspension was warmed to room temperature and stirred for 48 hours. The reaction was filtered, washed with isopropyl alcohol (15 mL), and dried to give 1-[2-(methylsulfanyl)phenyl]hydrazine hydrochloride (30 g, 93%). 1H NMR (CD3OD, 300 MHz) δ 7.44 (d, 1H, J=7.7 Hz), 7.32-7.26 (m, 1H), 7.08-7.00 (m, 2H), 2.39 (s, 3H) ppm.

1. additionadded dropwise to the suspension over 45 minutes
2. additionAfter the addition
3. additionadded slowly over 15 minutes to the reaction mixture
4. stirringstirred for 48 hours
5. filtrationThe reaction was filtered
6. washwashed with isopropyl alcohol (15 mL)
7. customdried

ORD record

ord-cc0a247dadd8430aaa2400a068bb8295

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592454B2