Water → 1-(2,4-Dichloroanilino)propan-2-one

HRID 254336Notes

Reaction equation

HRID 254336 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].I[CH2:11][C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][CH2:11][C:12](=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 111232,4-DichloroanilineHCID 11430Potassium CarbonateHCID 763962-Propanone, 1-iodo-

Product 1

HCID 220384831-(2,4-Dichloroanilino)propan-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4-dichloroaniline (20.2 g, 0.125 mol), iodoacetone (26.6 g, 0.145 mol) and potassium carbonate (18.1 g, 0.13 mol) in DMF (200 ml) was heated under nitrogen at 100° C. overnight. After cooling to rt, water was added and the mixture extracted with ether (×3). The combined organic extracts were washed with water, dried (Na2SO4), filtered and concentrated. Flash chromatography (Heptane:EtOAc 90: 10-80:20) afforded 13.6 g (50%) of the title compound as a brown solid.

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe mixture extracted with ether (×3)
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-10c8aaf252ae419bb64f7998616121c7
Source dataset
uspto-grants-2011_01
Patent number
US07875626B2

Reaction notes

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