Methyl iodide → HCID 13911212, compound

HRID 414868Notes

Reaction equation

HRID 414868 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:20])[C:18]=1[OH:19])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:6].[C:21]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:20][C:17]1[CH:16]=[C:4]([CH:3]=[C:2]([CH3:1])[C:18]=1[O:19][CH3:21])[C:5]([C:7]1[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13911211HCID 13911211, compound

Product 1

HCID 13911212HCID 13911212, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution containing compound 1 (15.0 g, 55.4 mmol), K2CO3 (20.0 g, 0.145 mol) and CH3I (30 mL, 0.48 mol) in 250 mL acetone was refluxed for 6 hours. The solvent was evaporated and the residue partitioned between CH2Cl2 and H2O. The organic layer was dried over Na2SO4, filtered and evaporated to leave a yellow-white powder. Recrystallization from CH3OH/pet ether at -20° C. gave 14.9 g of white crystals (94%) Tee material was characterized by NMR, TLC, mass spectroscopy, IR and elemental analysis, m.p. 131°-132.5° C. Anal. Calcd. for C16H15NO4 : C, 67.35; H, 5.31; N, 4.91. Found: C, 67.54; H, 5.38; N, 4.87.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe solvent was evaporated
  3. customthe residue partitioned between CH2Cl2 and H2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto leave a yellow-white powder
  8. customRecrystallization from CH3OH/pet ether at -20° C.

Sources & evidence

ORD record
ord-fb4d7235a75b4d7695c38adf4d6eac6f
Source dataset
uspto-grants-1988_12
Patent number
US04794191

Reaction notes

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