Reaction equation
Br[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[C:12]2[CH:13]=[C:14]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1.C(Cl)Cl.[CH3:33][OH:34]>[Ag]>[CH3:33][O:34][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[C:12]2[CH:13]=[C:14]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 3-[3-[3-(bromomethyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil(1.00 g, 1.99 mmol), methylene chloride and methanol is added silver trifluorormethanesulfonate. The resultant white suspension is stirred overnight at room temperature and filtered through a pad of diatomaceous earth with methylene chloride wash. The filtrate is washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to a pale yellow solid, which is recrystallized from diethyl ether to afford the title compound (0.790 g, 87.7%, mp 131-133° C.) which is identified by NMR spectral analysis.
Workup
- filtrationfiltered through a pad of diatomaceous earth with methylene chloride
- washwash
- washThe filtrate is washed with saturated sodium bicarbonate and brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo to a pale yellow solid, which
- customis recrystallized from diethyl ether
Sources & evidence
- ORD record
- ord-0e0b7e61abf743bc944f045de8b3f7a3
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706663B2
Linked notes
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