Thionyl Chloride → HCID 68074343, compound

HRID 517744Notes

Reaction equation

HRID 517744 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:21])([F:20])[C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17]([CH2:18]O)=[N:16][N:15]=[N:14]2)=[N:11][CH:12]=1>C1(C)C=CC=CC=1>[Cl:3][CH2:18][C:17]1[N:13]([C:10]2[CH:9]=[CH:8][C:7]([C:6]([F:21])([F:20])[F:5])=[CH:12][N:11]=2)[N:14]=[N:15][N:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66654834HCID 66654834, compound2×

Product 1

HCID 68074343HCID 68074343, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (0.22 g, 1.85 mmol) was added at room temperature to a solution of {1-[5-(Trifluoromethyl)-2-pyridinyl]-1H-tetrazol-5-yl}methanol (Intermediate 58, 0.20 g, 0.82 mmol) in toluene, and the reaction mixture was stirred for 2 hr at reflux. The reaction mixture was concentrated under vacuum. The residue was diluted with DCM and washed with ice-water, saturated NaHCO3 and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford the crude product. This was purified by column chromatography (60-120 mesh silica gel) eluting with 0-20% ethyl acetate/pet ether to give the title compound (60 mg) as a white powder.

Workup

  1. temperatureat reflux
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionThe residue was diluted with DCM
  4. washwashed with ice-water, saturated NaHCO3 and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customThis was purified by column chromatography (60-120 mesh silica gel)
  9. washeluting with 0-20% ethyl acetate/pet ether

Sources & evidence

ORD record
ord-31801dc0f202486589ae39f2bb171548
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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