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

HRID 552647Notes

Reaction equation

HRID 552647 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-748743f0cff047ada1bdfebcbee4303f
Source dataset
uspto-grants-2011_05
Patent number
US07951828B1

Reaction notes

Loading…