Stannous chloride dihydrate → 2-[(Trifluoromethyl)thio]aniline
Reaction equation
O.O.[Sn](Cl)Cl.[F:6][C:7]([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-])=O)([F:9])[F:8]>Cl.C(O)C>[F:6][C:7]([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])([F:9])[F:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A solution of 25.53 g of tin(II) chloride dihydrate in 40 ml of concentrated hydrochloric acid was added dropwise to a stirred solution of 5.05 g of 2-nitrophenyl trifluoromethyl sulfide, obtained according to Example 1, in 30 ml of ethanol. After the addition had ended, the mixture was heated to 100° C. and stirred at this temperature for 1.5 hours. The mixture was cooled, ethanol was evaporated off under reduced pressure, and the residue was poured into a mixture of 150 g of ice and 150 ml of 40% strength by weight aqueous sodium hydroxide solution. The product was extracted with ether. The combined ether extracts were dried over magnesium sulfate and concentrated under reduced pressure. Vacuum distillation of the residue gave 3.31 g (75.7% of theory) of 2-aminophenyl trifluoromethyl sulfide (boiling point 102-104° C. at 50 mbar, melting point: 30-31° C.).
Workup
- customobtained
- additionAfter the addition
- temperatureThe mixture was cooled
- customethanol was evaporated off under reduced pressure
- additionthe residue was poured into a mixture of 150 g of ice and 150 ml of 40% strength by weight aqueous sodium hydroxide solution
- extractionThe product was extracted with ether
- dry with materialThe combined ether extracts were dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- distillationVacuum distillation of the residue
Sources & evidence
- ORD record
- ord-3bf0986a95094df794209f16e30c6c5a
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06175042B1
Reaction notes
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