Water → HCID 11674176, compound

HRID 2247312Notes

Reaction equation

HRID 2247312 reaction equation
[CH:1]1([NH:7][C:8](=[O:20])[C:9]([S:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)([CH3:11])[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I[CH2:22][CH3:23].[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[CH:1]1([NH:7][C:8](=[O:20])[C:9]([S:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:22][CH3:23])=[CH:17][CH:18]=2)([CH3:11])[CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11709113HCID 11709113, compound

Product 1

HCID 11674176HCID 11674176, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Cyclohexyl-2-[(4-hydroxyphenyl)thio]-2-methylpropanamide (prepared as example 67) was dissolved in DMF and to the solution was added iodoethane. The solution was cooled in an ice-water bath and treated with NaH (60% in mineral oil). After stirring in the ice-water bath for half an hour and at rt for 2 h, water was added followed by EtOAc. After stirring for 10 min., the layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica, hexanes:EtOAc, 6:1) to provide the desired product as a white solid. LCMS: (M+H)+=322.2.

Workup

  1. temperatureThe solution was cooled in an ice-water bath
  2. customthe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica, hexanes:EtOAc, 6:1)

Sources & evidence

ORD record
ord-01063d0d4abc4d33913f010fc306810c
Source dataset
uspto-grants-2010_03
Patent number
US07687665B2

Reaction notes

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