Phosphorus oxychloride → 2-chloro-N-(4-chlorophenyl)-N-isopropyl-1-methyl-1H-benzimidazol-7-amine

HRID 2235556Notes

Reaction equation

HRID 2235556 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:20]([CH3:22])[CH3:21])[C:9]2[C:14]3[N:15]([CH3:19])[C:16](=O)[NH:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:16]1[N:15]([CH3:19])[C:14]2[C:9]([N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:20]([CH3:22])[CH3:21])=[CH:10][CH:11]=[CH:12][C:13]=2[N:17]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 685810587-[(4-Chlorophenyl)(isopropyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 685826702-chloro-N-(4-chlorophenyl)-N-isopropyl-1-methyl-1H-benzimidazol-7-amineYield 72%

Conditions

Temperature
80 °C

Procedure

A mixture of 7-[(4-chlorophenyl)(isopropyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (42 mg, 0.13 mmol) and phosphorous oxychloride (1.5 ml) was stirred at 80° C. for 1.5 h. The mixture was concentrated in vacuo and quenched with saturated aqueous sodium bicarbonate (10 ml) and extracted with ethyl acetate (20 ml). The extract was washed with water, dried over magnesium sulfate and evaporated. The residue was flash chromatographed eluting with a 17% ethyl acetate/hexanes to give 31.9 mg (72%) of the title compound as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customquenched with saturated aqueous sodium bicarbonate (10 ml)
  3. extractionextracted with ethyl acetate (20 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customchromatographed
  8. washeluting with a 17% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b162de6bb2434bf38b238c293eb15853
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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