Methyl iodide → HCID 71268159, compound

HRID 1519701Notes

Reaction equation

HRID 1519701 reaction equation
CI.[C:3](#N)C.[I:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:24])[NH:14][CH:15]([C:20]([NH:22][CH3:23])=[O:21])[C:16]([O:18][CH3:19])=[O:17])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C>[I:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:24])[NH:14][C:15]([CH3:3])([C:20]([NH:22][CH3:23])=[O:21])[C:16]([O:18][CH3:19])=[O:17])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 71268189HCID 71268189, compound

Product 1

HCID 71268159HCID 71268159, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.35 mL) was added to an acetonitrile (40 mL)-DMF (16 mL) suspension of 1-iodo-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl]carbamoyl}benzene (1.5 g) as obtained in Example 15-(1) and potassium carbonate (0.81 g), and the mixture was stirred for 4 days at room temperature under closed conditions. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and the desiccant was filtered out, whereafter the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=45/55→14/86) to obtain 1-iodo-4-{[1-methoxy-2-methyl-3-(methylamino)-1,3-dioxopropan-2-yl]carbamoyl}benzene (colorless oil) (1.3 g, 82%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered out, whereafter the solvent
  4. distillationwas distilled off under reduced pressure
  5. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=45/55→14/86)

Sources & evidence

ORD record
ord-27dfdf6bc4f9414e9f96a658c3a36017
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

Loading…