2-Chloroethanol → 5,6-Dichloro-2-(2-trifluoromethyl-[1,3]dioxolan-2-yl)-1H-benzimidazole

HRID 2405071Notes

Reaction equation

HRID 2405071 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.Cl[CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3([C:10]([F:13])([F:11])[F:12])[O:21][CH2:20][CH2:19][O:14]3)=[N:6][C:5]=2[CH:15]=1

Participants

6

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 166648615,6-Dichloro-2-(2-trifluoromethyl-[1,3]dioxolan-2-yl)-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(5,6-DiChloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (1.14 g; 4.02 mmol), 2-chloroethanol (0.83 mL; 12.4 mmol) and potassium carbonate (1.68 g; 12.2 mmol) were dissolved in DMF (18 mL). The reaction mixture was stirred for 18 hrs at ambient temperature, then diluted with ethyl acetate (80 mL), washed with water (50 mL) and brine (2×50 mL). The extracts were dried over Na2SO4, filtered, concentrated to a light brown solid and the light brown solid purified by column chromatography (SiO2; 30% ethyl acetate/hexanes) to yield the title compound as a tan solid.

Workup

  1. washwashed with water (50 mL) and brine (2×50 mL)
  2. dry with materialThe extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to a light brown solid
  5. customthe light brown solid purified by column chromatography (SiO2; 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c2fbd97537ba45798a4c78a748a99416
Source dataset
uspto-grants-2014_08
Patent number
US08802865B2

Reaction notes

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