2,6-Difluorobenzoyl isocyanate → 1-(2,5-Dimethyl-3-chloro-4-hydroxyphenyl)-3-(2,6-difluorobenzoyl)urea

HRID 569729Notes

Reaction equation

HRID 569729 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[C:4]([Cl:10])[C:3]=1[OH:11].[F:12][C:13]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:14]=1[C:15]([N:17]=[C:18]=[O:19])=[O:16]>ClCCl>[CH3:9][C:5]1[C:4]([Cl:10])=[C:3]([OH:11])[C:2]([CH3:1])=[CH:7][C:6]=1[NH:8][C:18]([NH:17][C:15](=[O:16])[C:14]1[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:13]=1[F:12])=[O:19]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 142756052,5-Dimethyl-6-chloro-4-aminophenol

Product 1

HCID 142756061-(2,5-Dimethyl-3-chloro-4-hydroxyphenyl)-3-(2,6-difluorobenzoyl)ureaYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a reaction flask containing 1.9 grams (11.0 mmol) of 2,5-dimethyl-6-chloro-4-aminophenol in 100 milliliters of dichloromethane was added 2.23 grams (12.2 mmol) of 2,6-difluorobenzoyl isocyanate. After stirring at ambient temperature for one hour, the resulting precipitate was filtered to afford 3.44 grams of 1-(2,5-dimethyl-3-chloro-4-hydroxyphenyl)-3-(2,6-difluorobenzoyl)urea having a melting point of 218° C.-219° C. Elemental analysis of the product indicated the following:

Workup

  1. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-01a50097b74e4942ad4cb1c3967c67d7
Source dataset
uspto-grants-1988_03
Patent number
US04734404

Reaction notes

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