Phosphorus oxychloride → HCID 67273157, compound

HRID 1698531Notes

Reaction equation

HRID 1698531 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[C:14]3[N:15]([CH3:19])[C:16](=O)[NH:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:24])=O>C(OCC)(=O)C>[Cl:24][C:16]1[N:15]([CH3:19])[C:14]2[C:9]([C:7]([C:6]3[CH:20]=[CH:21][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:8])=[CH:10][CH:11]=[CH:12][C:13]=2[N:17]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67272428HCID 67272428, compound

Product 1

HCID 67273157HCID 67273157, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 145 mg (0.514 mmol) of 7-(4-methoxybenzoyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one was dissolved in 1.5 mL of phosphorous oxychloride and heated at 100° C. for 18 h. The reaction was allowed to cool to room temperature and concentrated in vacuo. The residue thus obtained was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuo to give 124 mg (80%) of the title compound, which was used in the next step without further purification.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue thus obtained
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0af9bea6d29b41f5a2e20e4fe785046e
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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