Phosphorus oxychloride → HCID 68762626, compound

HRID 1398780Notes

Reaction equation

HRID 1398780 reaction equation
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13](=O)[NH:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:26])=O.C(=O)([O-])O.[Na+]>>[Cl:26][C:13]1[N:12]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[CH:9][C:10]=2[N:14]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 68760821HCID 68760821, compound

Product 1

HCID 68762626HCID 68762626, compoundYield 46%

Conditions

Temperature
100 °C

Procedure

The mixture of ethyl 4-[7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]butanoate (Reference Example 31; 1.94 g, 6.09 mmol) and phosphorus oxychloride (4.33 mL) was stirred at 100° C. for 2.5 hr. After cooling, the mixture was poured into ice water and neutralized with sodium hydrogen carbonate. The precipitate was removed by filtration and the filtrate was extracted with ethyl acetate (×3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless oil (942.6 mg, 2.80 mmol, 46%).

Workup

  1. temperatureAfter cooling
  2. customThe precipitate was removed by filtration
  3. extractionthe filtrate was extracted with ethyl acetate (×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a 0-15% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-a95e274a8a124ca491f091b0ec0197f5
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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