2,6-Difluorobenzoyl isocyanate → 1-[3-Chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl)-urea

HRID 846274Notes

Reaction equation

HRID 846274 reaction equation
[CH3:1][C:2]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[C:11]([CH3:12])=[CH:10][C:8]([NH2:9])=[C:7]([CH3:13])[C:6]=1[Cl:14].[F:20][C:21]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:22]=1[C:23]([N:25]=[C:26]=[O:27])=[O:24]>C1(C)C=CC=CC=1.CCCCCC>[Cl:14][C:6]1[C:7]([CH3:13])=[C:8]([NH:9][C:26]([NH:25][C:23](=[O:24])[C:22]2[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:21]=2[F:20])=[O:27])[CH:10]=[C:11]([CH3:12])[C:5]=1[O:4][C:3]1[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 148206063-Chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylaniline

Product 1

HCID 146260521-[3-Chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl)-urea

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

Into a solution of 4-(2,4-dimethylphenoxy)-2,5-dimethyl-3-chloroaniline (1.75 grams, 6.3 mmol) prepared in Part B in 7 milliliters of toluene, which solution was warmed to a temperature of 50° C., was added 1.14 grams (6.2 mmol) of 2,6-difluorobenzoyl isocyanate in 1.5 milliliters of toluene. The reaction mixture was heated to a temperature of 90° C. and maintained at this temperature for 0.5 hours. After cooling to room temperature, the reaction mixture was diluted with 20 milliliters of hexane and then cooled in an ice bath. A precipitate formed which was collected by filtration and washed with a cold solution of 50% hexane in toluene. After vacuum drying, a white solid (1.26 grams) which was identified as 1-[3-chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl)urea was obtained having a melting point of 183° C.-185° C. Elemental analysis of the white solid indicated the following:

Workup

  1. temperatureThe reaction mixture was heated to a temperature of 90° C.
  2. temperaturemaintained at this temperature for 0.5 hours
  3. temperatureAfter cooling to room temperature
  4. temperaturecooled in an ice bath
  5. customA precipitate formed which
  6. filtrationwas collected by filtration
  7. washwashed with a cold solution of 50% hexane in toluene
  8. customAfter vacuum drying
  9. customwas obtained

Sources & evidence

ORD record
ord-55ebad7888804c8a8dcb90dbe3957380
Source dataset
uspto-grants-1992_08
Patent number
US05135953

Reaction notes

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