Hydrochloric Acid → HCID 23729189, compound

HRID 2080625Notes

Reaction equation

HRID 2080625 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.[CH2:18](Br)[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[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])([CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=[CH2:18])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 98116BromomethylstyreneHCID 5359967IndiumHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 23729189HCID 23729189, 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; 1.04 mmol), cinnamyl bromide (1.6 mL; 10.5 mmol) and indium (1.22 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 oil. The crude oil was purified by column chromatography (SiO2; 20% 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 oil
  6. customThe crude oil was purified by column chromatography (SiO2; 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-174afbab5ecf4b10818a5b840cc75b8b
Source dataset
uspto-grants-2011_04
Patent number
US07932399B2

Reaction notes

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