Methyl iodide → HCID 22921562, compound

HRID 2258615Notes

Reaction equation

HRID 2258615 reaction equation
[CH2:1]([N:4]1[C:8]2[CH:9]=[C:10]([N:14]3[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[NH:16][C:15]3=[O:25])[C:11]([F:13])=[CH:12][C:7]=2[N:6]=[C:5]1[C:26]([F:29])([F:28])[F:27])[C:2]#[CH:3].[C:30](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:30][N:16]1[C:17]([C:21]([F:22])([F:23])[F:24])=[CH:18][C:19](=[O:20])[N:14]([C:10]2[C:11]([F:13])=[CH:12][C:7]3[N:6]=[C:5]([C:26]([F:27])([F:28])[F:29])[N:4]([CH2:1][C:2]#[CH:3])[C:8]=3[CH:9]=2)[C:15]1=[O:25]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22921576HCID 22921576, compound

Product 1

HCID 22921562HCID 22921562, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 0.6 gram (0.001 mole) of 3-[1-(2-propyn-1-yl)-2-trifluoromethyl-5-fluorobenzimidazol-6-yl]-6-trifluoromethyluracil, 0.4 gram (0.003 mole) of potassium carbonate, and 0.17 mL (0.003 mole) of methyl iodide in 30 mL of acetone was stirred at ambient temperature for about 18 hours, after which the reaction mixture was concentrated under reduced pressure to a residue. The residue was taken up in diethyl ether and washed 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 an oily residue, which was subjected to column chromatography on silica gel. Elution was accomplished using 1:3 ethyl acetate:hexane as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of 1-methyl-3-[1-(2-propyn-1-yl)-2-trifluoromethyl-5-fluorobenzimidazol-6-yl]-6-trifluoromethyluracil, mp 104°-105° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. concentrationafter which the reaction mixture was concentrated under reduced pressure to a residue
  2. washwashed with an aqueous solution saturated with sodium chloride
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to an oily residue, which
  6. washElution
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d33d3062659492bb7e64e7f1d176d1c
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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