Methyl iodide → HCID 9821004, compound

HRID 2299216Notes

Reaction equation

HRID 2299216 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH:12]2[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[C:4]([F:23])[CH:3]=1.CI.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:26])[S:9]([CH:12]2[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[C:4]([F:23])[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 9863761HCID 9863761, compound2×

Product 1

HCID 9821004HCID 9821004, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 6-[N-(4-chloro-2-fluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (Compound 1; 250 mg) obtained in Example 1 was 1.60 g) in N,N-dimethylformamide (2.5 ml), methyl iodide (118 mg), potassium carbonate (191 mg) were added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (30 ml), washed with water (30 ml×2) and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1/4) to yield ethyl 6-[N-(4-chloro-2-fluorophenyl)-N-methylsulfamoyl]-1-cyclohexene-1-carboxylate (Compound 2; 250 mg) as a colorless oil.

Workup

  1. washwashed with water (30 ml×2)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-dc15ec78a84747ed8771a61119ec074f
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

Loading…