p-Toluenesulfonic acid → HCID 86694705, compound

HRID 475146Notes

Reaction equation

HRID 475146 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:17](=[O:19])[CH3:18])[C:5]2[N:9]=[CH:8][N:7](C3CCCCO3)[C:6]=2[CH:16]=1.CC1C=CC(S(O)(=O)=O)=CC=1>O.CO>[F:1][C:2]1[CH:3]=[C:4]([C:17](=[O:19])[CH3:18])[C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 71272278HCID 71272278, compound

Product 1

HCID 86694705HCID 86694705, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)ethanone (1.0 g, 3.82 mmol) and TsOH (1.97 g, 11.45 mmol) in water (10 mL) and MeOH (50 mL) was heated at 80° C. for 3 h. The reaction mixture was quenched with EtOAc (50 mL) and water (50 mL). The aqueous phase was extracted with EtOAc (50 mL×2). The combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford 1-(6-fluoro-1H-benzo[d]imidazol-4-yl)ethanone as a yellow solid (678 mg, 99.8%). MS (ESI): m/z=179.3 [M+1].

Workup

  1. customThe reaction mixture was quenched with EtOAc (50 mL) and water (50 mL)
  2. extractionThe aqueous phase was extracted with EtOAc (50 mL×2)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fe6d9deaa5e49178199aa0f2c65f3f3
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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