Stannous Chloride → [2-(Methylsulfanyl)phenyl]hydrazine hydrochloride
Reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].[N:10]([O-])=O.[Na+].[Sn](Cl)[Cl:15]>Cl.FC(F)(F)C(O)=O.O>[ClH:15].[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10]Participants
Conditions
- Temperature
- 0 °C
Procedure
2-Methylsulfanyl-phenylamine (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 min. 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 min to the reaction mixture. The resultant suspension was warmed to rt and stirred for 48 h. The reaction was filtered, washed with iso-propyl 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.
Workup
- additionadded dropwise to the suspension over 45 min
- additionAfter the addition
- additionadded slowly over 15 min to the reaction mixture
- stirringstirred for 48 h
- filtrationThe reaction was filtered
- washwashed with iso-propyl alcohol (15 mL)
- customdried
Sources & evidence
- ORD record
- ord-a242244f678d4f8c92907621e2d91c81
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109339B2
Reaction notes
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