Thionyl Chloride → HCID 66654576, compound

HRID 517710Notes

Reaction equation

HRID 517710 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])[CH:9]=2)[N:6]=[N:5][N:4]=1.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[Cl:22][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])[CH:9]=2)[N:6]=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66654755HCID 66654755, compound2×

Product 1

HCID 66654576HCID 66654576, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile (Intermediate 23, 30.0 g) in toluene (500 mL) was added thionyl chloride (14.5 g, 0.122 mol) at room temperature. The reaction was heated to reflux and stirred for 2 hours. The reaction mixture was concentrated under vacuum and diluted with DCM. The resulting solution was washed with ice-water, followed by aqueous NaHCO3. The organic was separated and washed with brine solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by triturating with ether (500 mL) and dried under vacuum to yield 4-[5-(chloromethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile (23 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additiondiluted with DCM
  5. washThe resulting solution was washed with ice-water
  6. customThe organic was separated
  7. washwashed with brine solution
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified
  11. customby triturating with ether (500 mL)
  12. customdried under vacuum

Sources & evidence

ORD record
ord-0c26046ced6e4721819363caef52a8e3
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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