Ethylamine → N-ethyl-5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxamide
Reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:11][C:10]([C:12](Cl)=[O:13])=[CH:9][CH:8]=2)=[CH:5][C:4]([C:15]([F:18])([F:17])[F:16])=[N:3]1.C1COCC1.[CH2:24]([NH2:26])[CH3:25]>O>[CH2:24]([NH:26][C:12]([C:10]1[S:11][C:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:5]=2)=[CH:8][CH:9]=1)=[O:13])[CH3:25]Participants
5
Procedure
5-(1-Methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbonyl chloride (150 mg) and THF (2 ml) were added to a mixture of 70% ethylamine aqueous solution (1 ml) and THF (2 ml), followed by stirring at room temperature for 2 hours. Water was added to the reaction solution, the thus formed product was extracted with ethyl acetate and then the extract was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane to give N-ethyl-5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxamide (96 mg) as colorless powder crystals.
Workup
- extractionthe thus formed product was extracted with ethyl acetate
- washthe extract was washed with saturated brine
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under a reduced pressure
- customThe resulting residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane
Sources & evidence
- ORD record
- ord-6763f524af63444491b819ef3d32e7e0
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06958339B2
Reaction notes
Loading…