Phosphorus oxychloride → 2-chloro-4-methoxy-1H-Benzimidazole

HRID 1880082Notes

Reaction equation

HRID 1880082 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[NH:10][C:9](=O)[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:9]1[NH:10][C:11]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 129266284-methoxy-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 1784889662-chloro-4-methoxy-1H-Benzimidazole

Procedure

To a round bottomed flask was added 4-methoxy-1H-benzo[d]imidazol-2(3H)-one (1.8163 g, 11.06 mmol). POCl3 (1.031 mL, 11.06 mmol) was added and the reaction was brought to reflux. Upon completion, POCL3 was evaporated off. The residue was taken up in DCM. The reaction mixture was diluted with water and saturated sodium bicarbonate and extracted with DCM. The organic extract was washed with sat. sodium bicarbonate solution, water, brine, dried with magnesium sulfate, filtered, and concentrated to provide 2-Chloro-7-methoxy-1H-benzo[d]imidazole. MS (ESI, pos. ion) m/z: 182.9 (M+1).

Workup

  1. temperatureto reflux
  2. customUpon completion, POCL3 was evaporated off
  3. additionThe reaction mixture was diluted with water and saturated sodium bicarbonate
  4. extractionextracted with DCM
  5. extractionThe organic extract
  6. washwas washed with sat. sodium bicarbonate solution, water, brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2957171177ee4985b7e243588a9dc827
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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