Thionyl Chloride → HCID 66654660, compound

HRID 517718Notes

Reaction equation

HRID 517718 reaction equation
O[CH2:2][C:3]1[N:7]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[C:11]([NH2:13])=[O:12])[N:6]=[N:5][N:4]=1.S(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][CH2:2][C:3]1[N:7]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[C:11]([NH2:13])=[O:12])[N:6]=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 666547173-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-(trifluoromethyl)benzamide

Product 1

HCID 66654660HCID 66654660, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-(trifluoromethyl)benzamide (500 mg, 1.741 mmol) in toluene (5 mL) was added thionyl chloride (0.140 mL, 1.92 mmol) and the reaction heated to reflux for 4 hours. The reaction was allowed to cool and the solvent removed under vacuum. The residue was partitioned between DCM (20 mL) and water (10 mL). The organic layer collected via a hydrophobic frit and the solvent removed under vacuum. The residue was purified by silica chromatography (Biotage SP4, eluting 10% EtOAc in iso-hexane (5 column volumes) then a gradient from 10-100% EtOAc in iso-hexane (over 10 column volumes)) to yield the title compound as a pale yellow gum (360 mg).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 4 hours
  3. temperatureto cool
  4. customthe solvent removed under vacuum
  5. customThe residue was partitioned between DCM (20 mL) and water (10 mL)
  6. customThe organic layer collected via a hydrophobic frit
  7. customthe solvent removed under vacuum
  8. customThe residue was purified by silica chromatography (Biotage SP4
  9. washeluting 10% EtOAc in iso-hexane (5 column volumes)

Sources & evidence

ORD record
ord-1f723407aef34e0fb32174bcac07f368
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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