p-Toluenesulfonic acid → HCID 71272259, compound

HRID 475155Notes

Reaction equation

HRID 475155 reaction equation
[F:1][C:2]1[C:3]([C:11]#[N:12])=[CH:4][C:5]2[NH:9][CH:8]=[N:7][C:6]=2[CH:10]=1.[CH2:13]1[CH2:18][O:17][CH:16]=[CH:15][CH2:14]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[F:1][C:2]1[C:3]([C:11]#[N:12])=[CH:4][C:5]2[N:9]([CH:16]3[CH2:15][CH2:14][CH2:13][CH2:18][O:17]3)[CH:8]=[N:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 178509430HCID 178509430, compound

Product 1

HCID 71272259HCID 71272259, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 6-fluoro-3H-benzo[d]imidazole-5-carbonitrile (1.78 g, 11.1 mmol), DHP (1.84 g, 22.2 mmol), and TsOH (212 mg, 1.1 mmol) in THF (20 mL) under nitrogen was heated at 85° C. overnight. The reaction mixture was quenched with water (40 mL) and extracted with EtOAc (50 ml×2). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting petroleum ether:EtOAc (5:1) to afford 5-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-6-carbonitrile as white solid (2.0 g, 73.8%).

Workup

  1. customThe reaction mixture was quenched with water (40 mL)
  2. extractionextracted with EtOAc (50 ml×2)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting petroleum ether:EtOAc (5:1)

Sources & evidence

ORD record
ord-45369abb6e304cc4a141d732aaf4ab1b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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