Thionyl Chloride → HCID 66654350, compound

HRID 517740Notes

Reaction equation

HRID 517740 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:11]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][C:21]([F:24])([F:23])[F:22])[CH:13]=2)[N:10]=[N:9][N:8]=1>C1(C)C=CC=CC=1>[Cl:3][CH2:6][C:7]1[N:11]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][C:21]([F:24])([F:23])[F:22])[CH:13]=2)[N:10]=[N:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66654249HCID 66654249, compound2×

Product 1

HCID 66654350HCID 66654350, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (2.21 g, 18.6 mmol) was added to a stirred solution of 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-2-[(trifluoromethyl)oxy]benzonitrile (Intermediate 54, 3.50 g, 12.3 mmol) in toluene (50 mL) at room temperature, and the reaction mixture was heated to reflux for 4 h. The reaction mixture was concentrated under vacuum. The residue was diluted with DCM and washed with ice-cooled water, saturated aq NaHCO3 and brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. This was purified by column chromatography (60-120 mesh silica gel), eluting with 20% EtOAc/pet.ether to give the title compound as an off-white powder (2.85 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionThe residue was diluted with DCM
  5. washwashed with ice-
  6. temperaturecooled water, saturated aq NaHCO3 and brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto give the crude product
  10. customThis was purified by column chromatography (60-120 mesh silica gel)
  11. washeluting with 20% EtOAc/pet

Sources & evidence

ORD record
ord-038c62c72de24593ba5bfee57feec210
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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