Sodium Hydroxide → HCID 67273043, compound

HRID 1698544Notes

Reaction equation

HRID 1698544 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]2[N:15]([CH3:19])[C:16](=O)[NH:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH3:2].P(Cl)(Cl)([Cl:22])=O.[OH-].[Na+]>>[Cl:22][C:16]1[N:15]([CH3:19])[C:14]2[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH2:1][CH3:2])=[CH:10][CH:11]=[CH:12][C:13]=2[N:17]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 67272898HCID 67272898, compound

Product 1

HCID 67273043HCID 67273043, compoundYield 60%

Conditions

Temperature
80 °C

Procedure

A mixture of 190 mg (0.753 mmol) of 7-(2-ethylphenyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one and 1.5 mL of phosphorus oxychloride was stirred at 80° C. for 5 hours. After cooling, the reaction mixture was poured into ice and neutralized by 12 N sodium hydroxide. The aqueous suspension was extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 3-10% ethylacetate/n-hexane gradient mixture to give 123 mg (60%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into ice
  3. extractionThe aqueous suspension was extracted with ethyl acetate (X2)
  4. washThe combined organic layer was washed with brine (X1)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 3-10% ethylacetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-fae8eb71bb244c148d725b37a9193017
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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