Water → HCID 13242436, compound

HRID 1649303Notes

Reaction equation

HRID 1649303 reaction equation
[CH:1]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([OH:11])=[CH:3][C:2]=1[C:12]([F:15])([F:14])[F:13].[OH-].[K+].O.Cl[CH:20]([CH3:24])[C:21]([NH2:23])=[O:22]>CN(C)C=O>[F:15][C:12]([F:13])([F:14])[C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:7]([F:9])([F:8])[F:10])[CH:1]=1)[O:11][CH:20]([CH3:24])[C:21]([NH2:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 676803,5-Bis(trifluoromethyl)phenolHCID 943852-Chloropropanamide

Product 1

HCID 13242436HCID 13242436, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution containing 5 g (0.22 mole) of 3,5-ditrifluoromethylphenol, 1.6 g (0.024 mole) of 85% potassium hydroxide, 10 ml of water and 200 ml of N,N-dimethylformamide, 0.024 mole of 2-chloropropionamide was added in one portion. The stirred reaction mixture was heated at 120°-130° C. for 46 hours. After cooling to 0° C., 600 g of ice water was added and stirring continued at 0°-10° C. for 30 minutes. The resulting solid was collected by filtration, washed with water until neutral to litmus and air-dried at 25°-30° C. A product with a melting point of 84°-85° C. (determined after recrystallization from heptane) was obtained with a 48% yield.

Workup

  1. additionwas added in one portion
  2. customThe stirred reaction mixture
  3. temperaturewas heated at 120°-130° C. for 46 hours
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water until neutral to litmus and
  6. customair-dried at 25°-30° C
  7. customA product with a melting point of 84°-85° C. (determined after recrystallization from heptane)
  8. customwas obtained with a 48% yield

Sources & evidence

ORD record
ord-7f0072309dd74ad19f294c5f731d82fd
Source dataset
uspto-grants-1983_11
Patent number
US04416687

Reaction notes

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