Water → HCID 13242434, compound

HRID 1649301Notes

Reaction equation

HRID 1649301 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[CH2:20][C:21]([NH2:23])=[O:22]>CC(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][CH2:20][C:21]([NH2:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6580ChloroacetamideHCID 14797Potassium HydroxideHCID 676803,5-Bis(trifluoromethyl)phenol

Product 1

HCID 13242434HCID 13242434, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution containing 5 g (0.022 mole) of 3,5-ditrifluoromethylphenol, 1.6 g (0.024 mole) of 85% potassium hydroxide, 10 ml of water and 200 ml of acetone, 0.024 mole of chloroacetamide was added in one portion. The stirred reaction mixture was heated at 56°-60° C. for 22 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 139°-141° C. (determined after recrystallization from 6:1 mixture of heptane and isopropyl alcohol) was obtained with a 32% yield.

Workup

  1. additionwas added in one portion
  2. customThe stirred reaction mixture
  3. temperaturewas heated at 56°-60° C. for 22 hours
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water until neutral to litmus and air
  6. customdried at 25°-30° C
  7. customA product with a melting point of 139°-141° C. (determined after recrystallization from 6:1 mixture of heptane and isopropyl alcohol)
  8. customwas obtained with a 32% yield

Sources & evidence

ORD record
ord-def0a3d214474dafae96f11b97973ee0
Source dataset
uspto-grants-1983_11
Patent number
US04416687

Reaction notes

Loading…