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

HRID 1187977Notes

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-2e19a8447b3948e6931020d5deb5da34
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673951B2

Reaction notes

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