Water → 4-[5-(chloromethyl)-1H-tetrazol-1-yl]-3-methyl-2-(trifluoromethyl)benzonitrile
Reaction equation
O[CH2:2][C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[C:9]=2[CH3:20])[N:6]=[N:5][N:4]=1.S(Cl)([Cl:23])=O.O>ClCCl.CN(C)C=O>[Cl:23][CH2:2][C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[C:9]=2[CH3:20])[N:6]=[N:5][N:4]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-3-methyl-2-(trifluoromethyl)benzonitrile (Intermediate 48, 294 mg, 1.04 mmol) in dichloromethane (5 mL) and N,N-Dimethylformamide (0.5 mL), cooled in an ice bath under argon, was added dropwise thionyl chloride (0.080 mL, 1.09 mmol). The reaction was stirred at 25° C. for two hours. To the reaction was added water (50 mL) and DCM (100 mL) and the reaction partitioned through a hydrophobic frit. The organic layer was evaporated to dryness under vacuum to afford 240 mg of the title compound as a colourless oil.
Workup
- customthe reaction partitioned through a hydrophobic frit
- customThe organic layer was evaporated to dryness under vacuum
Sources & evidence
- ORD record
- ord-ade38453c0a24234be85a8463080936a
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115132B2
Reaction notes
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