Water → HCID 68074663, compound

HRID 517749Notes

Reaction equation

HRID 517749 reaction equation
O[CH2:2][C:3]1[N:7]([C:8]2[C:15]([CH3:16])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:9]=2)[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[C:15]([CH3:16])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:9]=2)[N:6]=[N:5][N:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 66654364HCID 66654364, compound2×

Product 1

HCID 68074663HCID 68074663, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-methyl-2-(trifluoromethyl)benzonitrile (Intermediate 63, 147 mg, 0.519 mmol) in dichloromethane (3 mL) and N,N-Dimethylformamide (0.5 mL), cooled in an ice bath under argon, was added dropwise thionyl chloride (0.040 mL, 0.545 mmol). The reaction was stirred at 25° C. for two hours. To the reaction was added water (20 mL) and DCM (50 mL) and the reaction partitioned through a hydrophobic frit. The organic layer was evaporated to dryness under vacuum to afford 133 mg of the title compound as a colourless oil.

Workup

  1. customthe reaction partitioned through a hydrophobic frit
  2. customThe organic layer was evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-1aa92ea35ad54675bfa3add42d10dc31
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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