Chloroacetone → HCID 60204538, compound

HRID 2267407Notes

Reaction equation

HRID 2267407 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:12]([CH:14]([C:25]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=O)[C:15]([S:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[S:16])#[N:13]>CN(C=O)C.CCOCC.O>[C:3]([C:2]1[S:16][C:15]([S:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[C:14]([C:12]#[N:13])[C:25]=1[C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 57428852HCID 57428852, compound

Product 1

HCID 60204538HCID 60204538, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Chloroacetone (0.100 mL, 1.26 mmol) was added dropwise to a stirred suspension of potassium carbonate (0.210 g, 1.52 mmol) and 4-fluorophenyl 2-cyano-3-(4-fluorophenyl)-3-oxopropanedithioate (0.20 g, 0.60 mmol) from step (ii) in DMF (2.5 mL). The reaction temperature was raised to 50° C. for 50 min. The reaction mixture was then diluted with Et2O and H2O. The organic layer was separated and washed with H2O and brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography, eluting with a gradient of 0.75-15% EtOAc/hexanes to afford the product as a yellow oil (102 mg, 0.27 mmol, 46% yield). MS (M−H)-370.

Workup

  1. customThe organic layer was separated
  2. washwashed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with a gradient of 0.75-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-1568ed8138894c2281a7e2043ee1384b
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…