Methyl iodide → HCID 20085201, compound

HRID 1608768Notes

Reaction equation

HRID 1608768 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1.CI>CN(C)C=O.C(C(C)=O)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[C:17]([O:19][CH3:1])=[O:18])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15790298HCID 15790298, compound

Product 1

HCID 20085201HCID 20085201, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a 3 liter flask stirring under nitrogen was charged 276 g (2.0 mole) of potassium carbonate and 1000 mL of methyl ethyl ketone. The mixture was stirred for 10 minutes, then a cloudy solution of 356 g (1.0 moles) of 4-(4-chlorophenyl)-2-phenyl-2-[(1,2,4-triazol-1-yl)-methyl]-butanoic acid in 2000 mL of dimethyl formamide was charged and stirred at room temperature for 30 minutes. To the mixture was added 284 g (2.0 moles) of methyl iodide in 125 mL of methyl ethyl ketone over 1 hour. The reaction was stirred at room temperature for 16 hours after which TLC indicated the reaction was complete. The solvent was removed under vacuum, then the residue was treated with 2000 mL of ethyl acetate and washed with 2×1000 mL of water, dried and concentrated. The residue crystallized on concentration and was washed several times with hexane, filtered and washed with additional hexane and gave 356 g (96% yield) of pale yellow solid, Example 127 of Table 1.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. stirringstirred at room temperature for 30 minutes
  3. stirringThe reaction was stirred at room temperature for 16 hours after which TLC
  4. customThe solvent was removed under vacuum
  5. additionthe residue was treated with 2000 mL of ethyl acetate
  6. washwashed with 2×1000 mL of water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue crystallized on concentration
  10. washwas washed several times with hexane
  11. filtrationfiltered
  12. washwashed with additional hexane

Sources & evidence

ORD record
ord-e9ce73bb36d545f482c36c33921877fe
Source dataset
uspto-grants-1995_03
Patent number
US05397768

Reaction notes

Loading…