Ethylene Glycol → HCID 178506272, compound

HRID 547644Notes

Reaction equation

HRID 547644 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]([NH:5][C:6]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]([O:16][C:17]2[CH:22]=[CH:21][C:20](C=O)=[CH:19][CH:18]=2)=[CH:8][C:7]=1[N+:25]([O-])=O)=O.[CH:30]([O:37][CH2:38][CH3:39])([O:34]CC)OCC.C(O)CO>C(OCC)(=O)C>[O:37]1[CH2:38][CH2:39][O:34][CH:30]1[C:20]1[CH:21]=[CH:22][C:17]([O:16][C:9]2[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[C:6]3[NH:5][C:3]([C:2]([F:29])([F:28])[F:1])=[N:25][C:7]=3[CH:8]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 57585938HCID 57585938, compound

Product 1

HCID 178506272HCID 178506272, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2,2,2-trifluoro-N-[4-[(4-formylphenyl)oxy]-2-nitro-6-(trifluoromethyl)phenyl]acetamide (0.65 g, 1.54 mmol), triethyl orthoformate (0.282 mL, 1.69 mmol), and ethylene glycol (0.343 mL, 6.16 mmol) was added (butyl)4NBr3 (0.007 g, 0.015 mmol). The reaction was stirred at ambient temperature for 1 hour and then diluted with ethyl acetate. The organics were washed 1×NaHCO3, 1× brine and then dried (Na2SO4), filtered and concentrated. The residue was dissolved in ethyl acetate (5 mL) and hydrogenated over 10% Palladium on carbon (0.13 g) under an atmosphere of hydrogen for 3 hours. The catalyst was removed by filtration through Celite and the filtrate concentrated. The residue was purified by silica gel column chromatography on using a gradient of 20-40% ethyl acetate:hexanes to give 5-{[4-(1,3-dioxolan-2-yl)phenyl]oxy}-2,7-bis(trifluoromethyl)-1H-benzimidazole.

Workup

  1. additionwas added (butyl)4NBr3 (0.007 g, 0.015 mmol)
  2. washThe organics were washed 1×NaHCO3, 1× brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethyl acetate (5 mL) and hydrogenated over 10% Palladium on carbon (0.13 g) under an atmosphere of hydrogen for 3 hours
  7. customThe catalyst was removed by filtration through Celite
  8. concentrationthe filtrate concentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ee35bf48bd744279b2716bf36b97c3c9
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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