Phosphorus oxychloride → Methyl 2-chloro-1-methyl-1H-benzimidazole-7-carboxylate

HRID 2235573Notes

Reaction equation

HRID 2235573 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=O.P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:3]1[N:2]([CH3:1])[C:6]2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59635373methyl 1-methyl-2-oxo-1,3-dihydro-2H-benzimidazole-7-carboxylate

Product 1

HCID 68581505Methyl 2-chloro-1-methyl-1H-benzimidazole-7-carboxylateYield 81%

Procedure

A solution of 2.00 g (9.70 mmol) of methyl 1-methyl-2-oxo-1,3-dihydro-2H-benzimidazole-7-carboxylate in 20 mL of phosphorous oxychloride was heated at 100° C. for 6 h. The reaction was concentrated in vacuo and the thus obtained residue was quenched with water and extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The thus obtained residue was purified via flash chromatography eluting with a solution of 20% ethyl acetate/hexanes to give 1.77 g (81%) of the title compound as white solids.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe thus obtained residue was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe thus obtained residue was purified via flash chromatography
  8. washeluting with a solution of 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-48e15f54a93b4bbba6363c49ba2406c2
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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