Hydrochloric Acid → HCID 23729482, compound

HRID 2037201Notes

Reaction equation

HRID 2037201 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]=[CH2:20].[In].Cl>C1COCC1>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]([OH:14])([CH2:20][CH:19]=[CH2:18])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 5359967IndiumHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 23729482HCID 23729482, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (1.41 g; 4.99 mmol), allyl bromide (0.85 mL; 10.05 mmol) and indium (1.15 g; 10.05 mmol) were suspended in THF (50 mL) and 0.01M HCl (150 mL) and stirred vigorously over 18 hours. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with brine (50 mL) and dried over Na2SO4. The resulting crude brown oil was purified by column chromatography (SiO2; 20% ethyl acetate/hexanes) to yield the title compound as a tan solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×30 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customThe resulting crude brown oil was purified by column chromatography (SiO2; 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ccdf71b9f3e44c249b9137ec092a4669
Source dataset
uspto-grants-2013_11
Patent number
US08575206B2

Reaction notes

Loading…