1,3-Dichloroacetone → HCID 12109865, compound

HRID 2084355Notes

Reaction equation

HRID 2084355 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH2:12])=[O:11])=[CH:4][CH:3]=1.[Cl:13][CH2:14][C:15]([CH2:17]Cl)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:13][CH2:14][C:15]1[N:12]=[C:10](/[CH:9]=[CH:8]/[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[O:11][CH:17]=1

Participants

5

Reactant 2

HCID 107931,3-DichloroacetoneHCID 966660HCID 966660, compound

Product 1

HCID 12109865HCID 12109865, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (E)-3-(4-methylphenyl)-2-propenamide (8.06 g) and 1,3-dichloroacetone (6.98 g) in toluene (50 ml) were refluxed for 3 hours. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water and saline, and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane 1:4) to yield the titled compound (8.44 g) as a white crystalline powder.

Workup

  1. temperaturewere refluxed for 3 hours
  2. temperatureAfter cooling
  3. washwashed with water and saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane 1:4)

Sources & evidence

ORD record
ord-db7e62e193fa4120884085b6cc3075dd
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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