Methyl iodide → HCID 22644724, compound

HRID 2084876Notes

Reaction equation

HRID 2084876 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[C:26](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH3:26])[C:16]2([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22644783HCID 22644783, compound

Product 1

HCID 22644724HCID 22644724, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)cyclohexanecarboxylate (4.5 g., 12.3 mmol), anhydrous potassium carbonate (20.0 g, excess) and methyl iodide (2 g, 14.08 mmol) was refluxed in acetone for sixteen hours. The reaction mixture was then cooled to room temperature and filtered. The acetone layer was concentrated and extracted with chloroform. The chloroform layer was washed well with water, dried over anhydrous MgSO4, filtered and concentrated to provide methyl 1-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]cyclohexanecarboxylate as a yellow oil. Yield: 4.6 g. (quantitative) Electrospray Mass Spec 380 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationThe acetone layer was concentrated
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed well with water
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d0be466a495c4d08ab0fdb6afa2a0afd
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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