Hexane → [2-[2-[[3-(Trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine
Reaction equation
[N+:1]([C:4]1[C:5]([S:10][CH2:11][CH2:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH4+].[Cl-].CCCCCC>C(O)C.[Zn]>[F:24][C:22]([F:23])([F:25])[C:18]1[CH:17]=[C:16]([S:13]([CH2:12][CH2:11][S:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=2)(=[O:14])=[O:15])[CH:21]=[CH:20][CH:19]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
1.31 g (20 mmol) zinc was added to a solution of 1.96 g (5.0 mmol) 3-nitro-2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]ethyl-sulfanyl]pyridine in ethanol (45 ml) and the mixture was cooled to 0° C. 200 ml (0.2 M, 40 mmol) of an aqueous NH4Cl solution were added at this temperature and then the mixture was heated for 30 min at 90° C. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with water and neutralised with NaHCO3. It was then extracted with EE and the organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 4:1) of the residue yielded 1.38 g (3.8 mmol, 76%) [2-[2-[[3-(trifluoromethyl)-phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine.
Workup
- temperaturethe mixture was heated for 30 min at 90° C
- concentrationThen the mixture was concentrated to small volume under vacuum
- extractionIt was then extracted with EE
- dry with materialthe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to small volume under vacuum
Sources & evidence
- ORD record
- ord-f375b2151ffd4c7badd07702ae9553e7
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247573B2
Reaction notes
Loading…