Methyl iodide → HCID 19082066, compound

HRID 963314Notes

Reaction equation

HRID 963314 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:24]=[C:23]([CH3:25])[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19](=O)[NH:20][CH:21]=3)=[C:10]([CH3:26])[CH:9]=2)[N:4]=1.CI.[C:31]([O-:34])([O-])=O.[K+].[K+]>COCCOCCN(CCOCCOC)CCOCCOC.CN(C=O)C>[F:27][C:2]([F:1])([F:28])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]([CH3:26])[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]3[C:31](=[O:34])[N:20]([CH3:21])[CH:19]=[CH:18][CH:17]=3)=[C:23]([CH3:25])[CH:24]=2)[N:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 190820095-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-2(1H)-pyridone

Product 1

HCID 19082066HCID 19082066, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.95 g (2.41 mmol) of 5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-2 (1H)-pyridone, 20 drops of TDA-1, and 0.5 ml of methyl iodide in 50 ml of dry DMF was added 0.96 g (3 eq) of milled K2CO3. The mixture was filtered and concentrated in vacuo to afford 0.9 g (91.8%) of 3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-1-methyl-2-pyridone, as a white solid, which was recrystallized from isopropyl acetate to yield a white solid, 143°-146° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56e8afbd9a0041fbba4f090e2548fb62
Source dataset
uspto-grants-1998_06
Patent number
US05763461

Reaction notes

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