Dichloromethane → N,N′-Bis[4-chloro-3-(trifluoromethyl)phenyl]urea

HRID 2110087Notes

Reaction equation

N[C:2]1O[N:5]=[C:4]([C:7]([CH3:10])(C)C)[CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][C:13]=1[C:21]([F:24])([F:23])[F:22].[CH2:25]([Cl:27])Cl>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:20])[NH:5][C:4]2[CH:7]=[CH:10][C:25]([Cl:27])=[C:2]([C:21]([F:24])([F:23])[F:22])[CH:3]=2)=[CH:14][C:13]=1[C:21]([F:22])([F:23])[F:24]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 5-amino-3-tert-butylisoxazole (0.100 g) in anh toluene (5 mL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.395 g). The reaction vessel was sealed, heated at 85° C. for 24 h, and cooled to room temp. The reaction mixture was added to a slurry of Dowex® 50WX2-100 resin (0.5 g) in CH2Cl2 (40 mL), and the resulting mixture was stirred vigorously for 72 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (gradient form 100% CH2Cl2 to 5% MeOH/95% CH2Cl2) to give bis(4-chloro-3-(trifluoromethyl)phenyl)urea followed by N-(3-tert-butyl-5-isoxazolyl)-N′-(4-chloro-3-(trifluoromethyl)phenyl)urea. The residue from the symmetrical urea fractions was triturated (Et2O/hexane) to give the urea as a white solid (0.110 g): TLC (3% MeOH/97% CH2Cl2) Rf 0.55; FAB-MS m/z 417 ((M+H)+). C. Urea Interconversions and Misc. Reactions C1. General Method for Alkylation of Hydroxyphenyl Ureas

Workup

customThe reaction vessel was sealed
temperaturecooled to room temp
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography (gradient form 100% CH2Cl2 to 5% MeOH/95% CH2Cl2)

Sources & evidence

ORD record: ord-3acf076f77fc46edb836d65e9c692f71
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517880B2

Reaction notes

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