Phosphorus oxychloride → 2-Chloro-7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1H-benzimidazole

HRID 1698585Notes

Reaction equation

HRID 1698585 reaction equation
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=O)[NH:14][C:10]=2[C:9]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:13]1[N:12]([CH3:16])[C:11]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[C:9]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[C:10]=2[N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 672733997-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1,3-dihydro-2H-benzimidazole-2-one

Product 1

HCID 672726412-Chloro-7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1H-benzimidazoleYield 52.2%

Conditions

Temperature
120 °C

Procedure

A mixture of 7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1,3-dihydro-2H-benzimidazole-2-one (79 mg, 0.278 mmol) in phosphorous oxychloride (0.78 ml, 8.33 mmol) was stirred at 120° C. for 2 h. The reaction was allowed to cool to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel with a 1-30% ethyl acetate/n-hexane gradient mixture to give 44 mg (0.145 mmol, 52%) of the title compound.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous saturated sodium bicarbonate and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel with a 1-30% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-ad01b4862c254ed391cb936db83979ab
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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