반응 #792152

반응 방정식

isopropylamine

product

1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

3-methylisatoic anhydride

→

N-[2-Methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

용매

dichloromethane

ether

pyridine

반응 조건

후처리

1. 1
   온도The resulting orange solution was cooled to 29° C.
2. 2
   기타The reaction mass exothermically
3. 3
   온도warmed to 39° C
4. 4
   온도It was further heated to 55° C. for a period of 30 minutes
5. 5
   기타whereupon much precipitate formed
6. 6
   세척The solution was washed with aqueous acid (5 mL of conc. HCl in 45 mL of water)
7. 7
   건조The organic layer was dried over MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated on a rotary evaporator
10. 10
    기타Upon reduction to ˜4 mL, product crystals had formed
11. 11
    기타precipitated
12. 12
    기타The product was isolated by filtration
13. 13
    세척washed with ether (2×10 mL)
14. 14
    세척washed with water (2×50 mL)
15. 15
    기타The wet cake was dried for 30 minutes at 70° C. in vacuo

실험 절차

A sample of 3-methylisatoic anhydride (0.30 g, 1.7 mmol) partially dissolved in pyridine (4.0 mL) was treated with 1-phenyl-3-(trifluoromethylpyrazole)-5-carboxyl chloride (i.e. the product of Step C) (0.55 g, 1.9 mmol). The mixture was heated to ˜95° C. for a period of 2 hours. The resulting orange solution was cooled to 29° C., then was treated with isopropylamine (1.00 g, 16.9 mmol). The reaction mass exothermically warmed to 39° C. It was further heated to 55° C. for a period of 30 minutes, whereupon much precipitate formed. The reaction mass was dissolved in dichloromethane (150 mL). The solution was washed with aqueous acid (5 mL of conc. HCl in 45 mL of water), then with aqueous base (2 g sodium carbonate in 50 mL of water). The organic layer was dried over MgSO4, filtered, then concentrated on a rotary evaporator. Upon reduction to ˜4 mL, product crystals had formed. The slurry was diluted with ˜10 mL of ether, whereupon more product precipitated. The product was isolated by filtration, washed with ether (2×10 mL), then washed with water (2×50 mL). The wet cake was dried for 30 minutes at 70° C. in vacuo. The product, a compound of the present invention, consisted of 0.52 g of an off-white powder melting at 260-262° C.

출처