Cesium carbonate → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine
Reaction equation
[OH:1][N:2]=[C:3]([N:10]1[C:14]([CH3:15])=[N:13][N:12]=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:22][C:23]1[S:24][CH:25]=[C:26]([CH2:28]Br)[N:27]=1>CC#N>[Br:22][C:23]1[S:24][CH:25]=[C:26]([CH2:28][O:1][N:2]=[C:3]([N:10]2[C:14]([CH3:15])=[N:13][N:12]=[N:11]2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:27]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of N-hydroxy-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine (2.0 g, 9.84 mmol, 1.0 eq.) in 50 ml of MeCN was added Cs2CO3 (3.52 g, 10.82 mmol, 1.2 eq.) followed by KI (0.163 g, 0.984 mmol, 0.1 eq.) in one portion. The resulting suspension was stirred for 5 mins before addition of 2-bromo-4-(bromomethyl)-1,3-thiazole (2.52 g, 9.84 mmol, 1 eq.) in one portion. The reaction was stirred for 24 hrs at room temperature. The solvent was evaporated then the residue was dissolved in EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine (3.3 g, 88% yield) as a yellow viscous oil.
Workup
- customThe solvent was evaporated
- dissolutionthe residue was dissolved in EtOAc
- washwashed with H2O
- customThe organic layer was separated
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-4bcb1ee92eee4493a3df100fcda67341
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466176B2
Reaction notes
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