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

HRID 552646Notes

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-4318827a3aff42879bcb1f913dc4c326
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951828B1

Reaction notes

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