Phosphorus oxychloride → Methyl 2,4-dichloro-1-methyl-1H-benzimidazole-7-carboxylate

HRID 1698577Notes

Reaction equation

HRID 1698577 reaction equation
[Cl:1][C:2]1[C:7]2[NH:8][C:9](=O)[N:10]([CH3:11])[C:6]=2[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:19])=O>C(OCC)(=O)C>[Cl:19][C:9]1[N:10]([CH3:11])[C:6]2[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67272570Methyl 7-chloro-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

Product 1

HCID 67272934Methyl 2,4-dichloro-1-methyl-1H-benzimidazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Methyl 7-chloro-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (150 mg, 0.63 mmol) was dissolved in 3 mL of phosphorous oxychloride and heated at 110° C. overnight. The reaction mixture was allowed to cool to room temperature, poured into a crushed ice, and stirred for 1 h. The resultant was diluted in ethyl acetate, washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuo. The obtained (147 mg, 90%) was used in the next reaction without further purification.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained (147 mg, 90%)
  7. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-298015aa55ab4d9d9d04662326f52a58
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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