반응 #1964425

반응 방정식

sodium carbonate

methyl 4-aminobenzoate

sodium iodide

sodium hydroxide

3-[chloro(cyclohexyl)methyl]-2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene

Hydrochloric acid

→

title compound

수율 71.3%

4-[(cyclohexyl{2-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}methyl)amino]benzoic acid

수율 71.3%

용매

N,N-dimethylacetamide

ethanol

tetrahydrofuran

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The extract was washed with saturated brine
5. 5
   건조dried over magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)
8. 8
   기타to give a pale-yellow oil
9. 9
   workup.STIRRINGthe mixture was stirred
10. 10
    온도with heated
11. 11
    온도under reflux for 4 hr
12. 12
    농축concentrated under reduced pressure
13. 13
    workup.DISSOLUTIONThe residue was dissolved in water (40 mL)
14. 14
    workup.ADDITION1N hydrochloric acid (20 mL) was added at 0° C
15. 15
    여과The resulting precipitate was collected by filtration

실험 절차

To a mixture of 3-[chloro(cyclohexyl)methyl]-2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene (1.27 g) synthesized above, methyl 4-aminobenzoate (1.03 g), sodium iodide (1.02 g) and N,N-dimethylacetamide (25 mL) was added sodium carbonate (721 mg), and the mixture was stirred overnight at 100° C. under an argon atmosphere. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give a pale-yellow oil. To a mixture of the obtained oil, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20 mL), and the mixture was stirred with heated under reflux for 4 hr, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), 1N hydrochloric acid (20 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title compound (1.15 g, 71%) as a white solid.

출처