Sulfuric Acid → HCID 22921535, compound

HRID 2258628Notes

Reaction equation

HRID 2258628 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[N:7]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[C:6]2[CH:13]=[C:14]([N:18]3[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]3=[O:30])[C:15]([F:17])=[CH:16][C:5]=2[N:4]=1.S(=O)(=O)(O)O.[CH3:38][CH:39](O)[CH3:40]>>[F:32][C:2]([F:1])([F:31])[C:3]1[N:7]([CH:8]([CH3:12])[C:9]([O:11][CH:39]([CH3:40])[CH3:38])=[O:10])[C:6]2[CH:13]=[C:14]([N:18]3[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[N:20]([CH3:29])[C:19]3=[O:30])[C:15]([F:17])=[CH:16][C:5]=2[N:4]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 22921548HCID 22921548, compound

Product 1

HCID 22921535HCID 22921535, compound

Procedure

A stirred mixture of 0.7 gram (0.002 mole) of 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl)benzimidazol-1-yl]propanoic acid, 0.1 mL of concentrated sulfuric acid, and 1.0 gram of molecular sieves (synthetic zeolites, 4 to 8 mesh, pore size 4 angstroms) in 1-methylethanol was heated at reflux for about 18 hours. After this time, the reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was dissolved in ethyl acetate and washed with an aqueous solution saturated with sodium bicarbonate and then with an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil, which was triturated with petroleum ether, yielding solid 1-methylethyl 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl)benzimidazol-1-yl]propanoate, mp 133°-135° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  3. temperatureAfter this time, the reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure to a residue
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with an aqueous solution saturated with sodium bicarbonate
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a residual oil, which
  10. customwas triturated with petroleum ether

Sources & evidence

ORD record
ord-5d90e85dbcf84f1b9971d23e079a649a
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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