Potassium Carbonate → 5,6-Dichloro-2-(2-trifluoromethyl-oxazolidin-2-yl)-1H-benzimidazole

HRID 2273301

Reaction equation

HRID 2273301 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.Br.Br[CH2:20][CH2:21][NH2:22].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])[NH:22][CH2:21][CH2:20][O:14]3)=[N:6][C:5]=2[CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27742172-Bromoethylamine hydrobromideHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 583331665,6-Dichloro-2-(2-trifluoromethyl-oxazolidin-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 (594 mg), 2-bromoethylamine-hydrobromide (860 mg) and potassium carbonate (871 mg) were dissolved in DMF (5 mL). The reaction mixture was stirred for 18 hrs at ambient temperature, then diluted with ethyl acetate (50 mL), washed with water (50 mL) and brine (2×20 mL). The extracts were dried over Na2SO4, filtered, concentrated, and purified by column chromatography (SiO2; 40% ethyl acetate/hexanes) to yield the title compound as a yellow solid.

Workup

  1. washwashed with water (50 mL) and brine (2×20 mL)
  2. dry with materialThe extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (SiO2; 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d011aad0429f4f5d848c8bbf7673881c
Source dataset
uspto-grants-2015_09
Patent number
US09120830B2

Linked notes

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