Water → HCID 178521819, compound

HRID 2263030Notes

Reaction equation

HRID 2263030 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([NH2:12])=[CH:11][C:5]=2[N:4]=1.N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23].O>O1CCCC1>[F:14][C:2]([F:1])([F:13])[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([NH:12][C:22](=[O:23])[O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[CH:11][C:5]=2[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 178507351HCID 178507351, compound

Product 1

HCID 178521819HCID 178521819, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(trifluoromethyl)-1H-benzimidazol-5-amine (1.00 g, 4.97 mmol) and pyridine (0.473 ml, 5.97 mmol) in tetrahydrofuran (17 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (0.826 ml, 5.97 mmol), and the mixture was stirred at room temperature for 1 hour and half. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to give 1.28 g (68.5%) of the desired product as a solid.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-f0dd0b3b0b54483d90d5c33375b1703c
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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