Chloroacetyl isocyanate → N-chloroacetyl-N'-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]-N'-methyl urea

HRID 878828Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([NH:20][CH3:21])=[O:19])=[C:16]([CH3:24])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:29][CH2:30][C:31]([N:33]=[C:34]=[O:35])=[O:32]>C1(C)C=CC=CC=1>[Cl:29][CH2:30][C:31]([NH:33][C:34]([N:20]([C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:24])[CH3:21])=[O:35])=[O:32]

Participants

Conditions

Temperature: 50 °C

Procedure

In a solution of 0.86 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-methyl benzoic acid amide in 10 mL of toluene, 0.36 g of chloroacetyl isocyanate was added, and stirred at 50° C. for 24 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (gradient of 0:1 to 3:2) to obtain 0.93 g of the aimed product as colorless oily substance.

Workup

customAfter the completion of the reaction
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record: ord-e6c96ed979ac45ddbc5293ffd8641084
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987464B2

Reaction notes

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