Hydrochloric Acid → HCID 23729507, compound

HRID 2037214Notes

Reaction equation

HRID 2037214 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[CH2:19][C:20](=[CH2:24])[C:21]([OH:23])=[O:22].[In].Cl>C1COCC1.O.C(OCC)(=O)C>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]([OH:14])([C:10]([F:13])([F:11])[F:12])[CH2:24][C:20](=[CH2:19])[C:21]([OH:23])=[O:22])=[N:6][C:5]=2[CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5588842-(Bromomethyl)propenoic acidHCID 5359967IndiumHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 23729507HCID 23729507, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (0.30 g; 1.05 mmol), 2-(bromomethyl)acrylic acid (1.80 g; 10.9 mmol) and indium (1.23 g; 10.7 mmol) were suspended in THF (10 mL) and 0.02 M HCl (15 mL) and stirred vigorously over 18 hours. The reaction mixture was then diluted with water (60 mL) and ethyl acetate (40 mL), the layers were separated and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined extracts were washed with brine (50 mL) and dried over Na2SO4 to yield a crude material. The crude material was purified by column chromatography (SiO2; 50% ethyl acetate/hexanes) to yield the title compound as an off-white solid.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customto yield a crude material
  6. customThe crude material was purified by column chromatography (SiO2; 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-382ff57e4aa64cf79453b5c3089ad021
Source dataset
uspto-grants-2013_11
Patent number
US08575206B2

Reaction notes

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