Phosphorus oxychloride → HCID 68582683, compound

HRID 2235576Notes

Reaction equation

HRID 2235576 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([NH:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=O.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:3]1[N:2]([CH3:1])[C:6]2[C:7]([NH:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68581157HCID 68581157, compound

Product 1

HCID 68582683HCID 68582683, compoundYield 45%

Procedure

A mixture of 4-[(1-methyl-2-oxo-1,3-dihydro-2H-benzimidazol-7-yl)amino]benzonitrile (137 mg, 0.518 mmol), prepared in a similar manner as described in Example 154, and phosphorous oxychloride (1.5 ml) was refluxed for 3 h. The mixture was concentrated in vacuo and quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated. The residue was flash chromatographed eluting with a solution of 25% ethyl acetate/hexane to give 66 mg (45%) of the title compound.

Workup

  1. customprepared in a similar manner
  2. temperaturewas refluxed for 3 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customquenched with saturated aqueous sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customchromatographed
  10. washeluting with a solution of 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2f4a9e33b1634766817e2caa1c0cbb4c
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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