Methyl iodide → HCID 22644724, compound

HRID 2414583Notes

Reaction equation

HRID 2414583 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>[CH3:25][O:24][C:22]([C:16]1([N:15]([S:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[CH3:26])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:23]

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 methyl1-[{[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-da294991cfa14296a027742db16e5f2f
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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