Epichlorohydrin → HCID 5328503, compound

HRID 324279Notes

Reaction equation

HRID 324279 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH2:19]([CH:21]1[O:23][CH2:22]1)Cl>C1COCC1.CN(C=O)C>[O:23]1[CH2:22][CH:21]1[CH2:19][O:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 6676621-Phenyl-1H-benzimidazol-5-ol

Product 1

HCID 5328503HCID 5328503, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A solution of 5-hydroxy-1-phenylbenzimidazole (Example 14) (0.24 g, 1.14 mmol) 1:1 THF/DMF (5 mL) was added under nitrogen to a stirred suspension of sodium hydride (41 mg of a 60% dispersion in oil, 1.71 mmol). After 5 minutes, epichlorohydrin (98 μL, 1.26 mmol) was added, and the solution was refluxed for 4 hours. The cooled solution was partitioned between diethyl ether and water, and the extract was washed with 2N NaOH and worked up to give an oil which was chromatographed on silica gel. EtOAc/petroleum ether (1: 1) eluted foreruns, while EtOAc eluted the epoxide Example 34 (0.14 g, 46%): mp (EtOAc/petroleum ether) 96-97.5° C.

Workup

  1. temperaturethe solution was refluxed for 4 hours
  2. customThe cooled solution was partitioned between diethyl ether and water
  3. washthe extract was washed with 2N NaOH
  4. customto give an oil which
  5. customwas chromatographed on silica gel
  6. washEtOAc/petroleum ether (1: 1) eluted foreruns
  7. washwhile EtOAc eluted the epoxide Example 34 (0.14 g, 46%)
  8. custommp (EtOAc/petroleum ether) 96-97.5° C.

Sources & evidence

ORD record
ord-07e58b24c2a646f7b16f360f4ad474d2
Source dataset
uspto-grants-2001_04
Patent number
US06218388B1

Reaction notes

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