Tetrahydropyran → HCID 86694696, compound

HRID 475100Notes

Reaction equation

HRID 475100 reaction equation
[CH2:1]([C:3]1[C:11]2[N:10]=[CH:9][NH:8][C:7]=2[CH:6]=[CH:5][C:4]=1[C:12]#[N:13])[CH3:2].[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][O:14]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[C:12]#[N:13])[CH3:2]

Participants

5

Reactant 3

HCID 8894TetrahydropyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86694695HCID 86694695, compound

Product 1

HCID 86694696HCID 86694696, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-ethyl-1H-benzo[d]imidazole-5-carbonitrile (6.8 g, 0.04 mol) in dry toluene (70 mL) was added tetrahydro-2H-pyran (10.53 g, 0.12 mol, 3 equiv.) and pyridinium-p-toluenesulfonate (4 g, 0.02 mol, 0.5 equiv.) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was concentrated, quenched with water and extracted with EtOAc. The combined organic layers were washed with brine and then dried (Na2SO4), filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with 50% EtOAc/hexane to afford 4-ethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrile (7 g, 69% yield) as a yellow oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationThe reaction mixture was concentrated
  4. customquenched with water
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by SiO2 chromatography
  11. washeluting with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-6277db1e044a40ad81707776b828051b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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