Triethylamine → N-Carbamoyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-methyl benzoic acid amide

HRID 1187978Notes

Reaction equation

HRID 1187978 reaction equation
ClCC([NH:5][C:6]([N:8]([C:10](=[O:35])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:21][C:20]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=3)([C:22]([F:25])([F:24])[F:23])[O:19][N:18]=2)=[CH:13][C:12]=1[CH3:34])[CH3:9])=[O:7])=O.C(N(CC)CC)C>CO>[C:6]([N:8]([CH3:9])[C:10](=[O:35])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:21][C:20]([C:26]3[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=3)([C:22]([F:25])([F:23])[F:24])[O:19][N:18]=2)=[CH:13][C:12]=1[CH3:34])(=[O:7])[NH2:5]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86654461N-chloroacetyl-N'-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]-N'-methyl urea

Product 1

HCID 66784361N-Carbamoyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-methyl benzoic acid amideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.40 g of N-chloroacetyl-N′-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]-N′-methyl urea synthesized in Synthetic Example 27 and 0.04 g of triethylamine in 4 mL of methanol was stirred at room temperature for 2 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 1:4 to 4:1) to obtain 0.31 g of the aimed product as white crystal.

Workup

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

Sources & evidence

ORD record
ord-2461f929422a4432b30d3359bddbff32
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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