2,6-Dimethoxybenzoyl chloride → N-[5-(1-Ethylcyclohexyl)-1,2-oxazol-3-yl]-2,6-dimethoxybenzamide
Reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2([CH2:13][CH3:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[O:4][N:3]=1.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:18]=1[C:19](Cl)=[O:20]>C1(C)C=CC=CC=1.ClCCl>[CH2:13]([C:7]1([C:5]2[O:4][N:3]=[C:2]([NH:1][C:19](=[O:20])[C:18]3[C:22]([O:26][CH3:27])=[CH:23][CH:24]=[CH:25][C:17]=3[O:16][CH3:15])[CH:6]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:14]Participants
5
Procedure
A solution of 14 g of 3-amino-5-(1-ethylcyclohexyl)isoxazole and 14.4 g of 2,6-dimethoxybenzoyl chloride in 100 ml of toluene was heated to reflux and stirred for eighteen hours. The reaction mixture then was cooled to room temperature and the solvent was removed by evaporation under reduced pressure to provide a solid. The solid was dissolved in 200 ml of dichloromethane, washed with dilute sodium hydroxide and with brine, dried, and the solvent was removed by evaporation. The product was crystallized from dichloromethane and diethyl ether to provide 15.5 g of N-[5-(1-ethylcyclohexyl)-3-isoxazolyl]-2,6-dimethoxybenzamide. M.P. 179°-181° C. Yield 60%.
Workup
- temperatureto reflux
- customthe solvent was removed by evaporation under reduced pressure
- customto provide a solid
- washwashed with dilute sodium hydroxide and with brine
- customdried
- customthe solvent was removed by evaporation
- customThe product was crystallized from dichloromethane and diethyl ether
Sources & evidence
- ORD record
- ord-984955cb20b94f86aa6322578f4c0f0b
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05086184
Reaction notes
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