Sulfuric Acid → HCID 22921548, compound

HRID 2258627Notes

Reaction equation

HRID 2258627 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[N:7]([CH:8]([CH3:11])[CH2:9][OH:10])[C:6]2[CH:12]=[C:13]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])[C:14]([F:16])=[CH:15][C:5]=2[N:4]=1.[Cr](O)(O)(=O)=[O:33].S(=O)(=O)(O)O>CC(C)=O.O.[O-2].[O-2].[O-2].[Cr+6]>[F:31][C:2]([F:1])([F:30])[C:3]1[N:7]([CH:8]([CH3:11])[C:9]([OH:33])=[O:10])[C:6]2[CH:12]=[C:13]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:26])([F:25])[F:27])[N:19]([CH3:28])[C:18]3=[O:29])[C:14]([F:16])=[CH:15][C:5]=2[N:4]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 22921546HCID 22921546, compound

Product 1

HCID 22921548HCID 22921548, compound

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, 4.3 grams (0.010 mole) of 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl) benzimidazol-1-yl]propan-1-ol in 120 mL of acetone was stirred, and 16 mL chromic acid (prepared by dissolving about five grams of chromium trioxide in 12 mL of water, then adding five mL of concentrated sulfuric acid), was added dropwise during a one hour period. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for about 18 hours. The reaction was quenched with about three mL of 1-methylethanol, and the mixture was made basic with an aqueous solution saturated with sodium bicarbonate. The mixture was filtered to remove chromium salts, and the filtrate was extracted with ethyl acetate. The combined extracts were then washed with an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 3.0 grams of 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl)benzimidazol-1-yl]propanoic acid. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added dropwise during a one hour period
  2. additionUpon completion of the addition
  3. customThe reaction was quenched with about three mL of 1-methylethanol
  4. filtrationThe mixture was filtered
  5. customto remove chromium salts
  6. extractionthe filtrate was extracted with ethyl acetate
  7. washThe combined extracts were then washed with an aqueous solution saturated with sodium chloride
  8. dry with materialThe organic layer was dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a716e5b344ee4d48861868ff18c1b59d
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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