Hexane → HCID 18789823, compound

HRID 1638751Notes

Reaction equation

HRID 1638751 reaction equation
[Cl:1][C:2]1[C:3]([CH3:19])=[C:4]([CH:6]=[C:7]([CH3:18])[C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])[NH2:5].[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].CCCCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:19])=[C:4]([NH:5][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:6]=[C:7]([CH3:18])[C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17]

Participants

5

Reactant 3

HCID 8058HexaneHCID 27333692,6-Difluorobenzoyl isocyanateHCID 19841463HCID 19841463, compound

Product 1

HCID 18789823HCID 18789823, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a magnetically stirred solution of 3-chloro-4-(2,4-dichlorophenoxy)-2,5-dimethylaniline (1.5 grams, 4.73 mmol) prepared in Part B in toluene (15 milliliters) under nitrogen atmosphere was added neat 2,6-difluorobenzoyl isocyanate (1.3 grams, 7.10 mmol) and the mixture was refluxed for a period of 1 hour. The reaction mixture was allowed to cool and hexane (3 milliliters) was added to induce crystallization. The resultant precipitate was filtered and washed successively with hexane and toluene to give pure 1-[3-chloro-4-(2,4-dichlorophenoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl) urea (2.29 grams, 4.58 mmol, 97%) as a white solid having a melting point of 188° C.-190° C. Elemental analysis of the white solid indicated the following:

Workup

  1. temperaturethe mixture was refluxed for a period of 1 hour
  2. temperatureto cool
  3. customcrystallization
  4. filtrationThe resultant precipitate was filtered
  5. washwashed successively with hexane and toluene

Sources & evidence

ORD record
ord-92975ddeb48043748219a25b8ee96168
Source dataset
uspto-grants-1989_11
Patent number
US04880838

Reaction notes

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