Methanol → HCID 178440127, compound
Reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[C:6]([C:17]([C:23]([F:26])([F:25])[F:24])([C:19]([F:22])([F:21])[F:20])[NH2:18])[NH:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12](SC)=[CH:11][CH:10]=1)[CH3:3].O[O:28][S:29]([O-:31])=O.[K+].S(OOS([O-])(=O)=O)(O)(=O)=O.[K+].[CH3:44]O>>[CH3:1][CH:2]([C:4]1[N:5]=[C:6]([C:17]([C:23]([F:26])([F:24])[F:25])([C:19]([F:20])([F:21])[F:22])[NH2:18])[NH:7][C:8]=1[C:9]1[CH:10]=[CH:11][C:12]([S:29]([CH3:44])(=[O:31])=[O:28])=[CH:13][CH:14]=1)[CH3:3]Participants
5
Procedure
A mixture of 1.8 g (4.5 mmoles) of 4-(1-methylethyl)-5-(4-methylthiophenyl)-α,α-bis(trifluoromethyl)-1H-imidazole-2-methanamine, 7.25 g (11.8 mmoles) of Oxone® (potassium hydrogen persulfate) and 50 ml of methanol were stirred together overnight. The solid was filtered off and the filtrate was evaporated in vacuo. The residue was partitioned between ethyl acetate and water and the layers were separated. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford 2.1 g of an oil. The product was purified via flash chromatography on silica gel (73:27 hexane/ethyl acetate) to afford 1.02 g (53%) of the title compound as an off-white crystalline solid, m.p. 155°-157° C.
Workup
- filtrationThe solid was filtered off
- customthe filtrate was evaporated in vacuo
- customThe residue was partitioned between ethyl acetate and water
- customthe layers were separated
- washThe organic layer was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2ddad78127a04d1fa487356fe01948d8
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04632930
Reaction notes
Loading…