Phosphorus oxychloride → HCID 67273736, compound

HRID 1698547Notes

Reaction equation

HRID 1698547 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([N:11]3[CH:15]=[CH:14][C:13]([CH3:16])=[N:12]3)=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=O.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:3]1[N:2]([CH3:1])[C:6]2[C:7]([N:11]3[CH:15]=[CH:14][C:13]([CH3:16])=[N:12]3)=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67272752HCID 67272752, compound

Product 1

HCID 67273736HCID 67273736, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 17 mg (0.0745 mmol) of 1-methyl-7-(3-methyl-1H-pyrazol-1-yl)-1,3-dihydro-2H-benzimidazol-2-one in 0.5 mL of phosphorus oxychloride was stirred at 80° C. for 5 days. After cooling, phosphorus oxychloride was evaporated in vacuo. The residue was neutralized by 12 N aqueous sodium hydroxide. The aqueous suspension was extracted with ethyl acetate (X2). The combined organic layer was washed with water (X1) and brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC eluting with a 30% ethylacetate/n-hexane mixture to give 2-chloro-1-methyl-7-(3-methyl-1H-pyrazol-1-yl)-1H-benzimidazole. A mixture 2-chloro-1-methyl-7-(3-methyl-1H-pyrazol-1-yl)-1H-benzimidazole obtained above, 48 mg (0.223 mmol) of 4-bromo-2-methoxy-6-methylaniline and 0.15 mL of 1-methyl-2-pyrrolidinone was stirred at 120° C. for 3 days. After cooling, the reaction mixture was neutralized by saturated aqueous sodium hydrogen carbonate. The aqueous suspension was extracted with ethyl acetate (X2). The combined organic layer was washed with water (X1) and brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC eluting with a 75% ethylacetate/n-hexane mixture to give 5.7 mg (18%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. customphosphorus oxychloride was evaporated in vacuo
  3. extractionThe aqueous suspension was extracted with ethyl acetate (X2)
  4. washThe combined organic layer was washed with water (X1) and brine (X1)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC
  8. washeluting with a 30% ethylacetate/n-hexane mixture

Sources & evidence

ORD record
ord-e3f4452c11a145b7b4300b9cd25f71fc
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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