Water → HCID 11522809, compound

HRID 2247311Notes

Reaction equation

HRID 2247311 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.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]#[N:30].O>CN(C=O)C>[C:29]([CH2:28][O:19][C:16]1[CH:15]=[CH:14][C:13]([S:12][C:9]([CH3:11])([CH3:10])[C:8]([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:20])=[CH:18][CH:17]=1)#[N:30]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 11709113HCID 11709113, compound

Product 1

HCID 11522809HCID 11522809, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-Cyclohexyl-2-[(4-hydroxyphenyl)thio]-2-methylpropanamide (prepared as example 67) was dissolved in DMF and to this was added potassium carbonate and bromoacetonitrile and the resulting solution was heated to 80° C. for 2 h. The reaction mixture was poured into water and extracted with EtOAC, dried over MgSO4 and concentrated. The product was purified by flash chromatography, eluting with hexane/EtOAc, to provide 19.4 mg of the desired product. LCMS: (M+H)+=333.2.

Workup

  1. extractionextracted with EtOAC
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe product was purified by flash chromatography
  5. washeluting with hexane/EtOAc

Sources & evidence

ORD record
ord-df2855c5673641e2a568a17dbbefbed9
Source dataset
uspto-grants-2010_03
Patent number
US07687665B2

Reaction notes

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