Ethanol → Pentanamide, 2-chloro-N-(2,4-dichlorophenyl)-4,4-dimethyl-3-oxo-

HRID 2254538Notes

Reaction equation

HRID 2254538 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][C:7]([CH3:23])([CH3:22])[C:8](=[O:21])[CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])=[O:11].C(O)C>ClCCl>[Cl:4][CH:9]([C:8](=[O:21])[C:7]([CH3:23])([CH3:22])[CH3:6])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])=[O:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 24648Sulfuryl chlorideHCID 113064Pentanamide, N-(2,4-dichlorophenyl)-4,4-dimethyl-3-oxo-

Product 1

HCID 112507Pentanamide, 2-chloro-N-(2,4-dichlorophenyl)-4,4-dimethyl-3-oxo-Yield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Sulfuryl chloride (54.1 g, 0.4 mol) was added dropwise with vigorous stirring over a 60 minute period to a solution of N-[4,4-dimethyl-3-oxopentanoyl]-2,4-dichloroaniline, prepared as above (109 g, 0.378 mol) in dichloromethane (600 mL) at -10° C. The reaction mixture was maintained at this temperature for 3 hours after the addition had been completed. After this time, the mixture was allowed to warm to 0° C. and ice (approximately 50 mL) was added, with stirring. The organic layer was separated and washed with 50% saturated aqueous sodium chloride solution (2×500 mL), then dried over magnesium sulfate. Evaporation of the solvent afforded a brown oil which was stirred with ethanol (150 mL) to induce crystallization of the product. The resultant mixture was stored at 0° C. overnight. The solid product was removed by filtration, washed with cold ethanol and dried to afford N-[2-chloro-4,4,-dimethyl-3-oxopentanoyl]-2,4-dichloroaniline (104.2 g, 85.4% yield) as a white crystalline solid which melted at 64.5°-65.5° C. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

  1. temperatureThe reaction mixture was maintained at this temperature for 3 hours
  2. additionafter the addition
  3. customThe organic layer was separated
  4. washwashed with 50% saturated aqueous sodium chloride solution (2×500 mL)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customafforded a brown oil which
  8. customcrystallization of the product
  9. customThe solid product was removed by filtration
  10. washwashed with cold ethanol
  11. customdried

Sources & evidence

ORD record
ord-d5d224a093de4db983f991764ff90ca7
Source dataset
uspto-grants-1993_08
Patent number
US05236884

Reaction notes

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