反応 #792152

反応方程式

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

溶媒

dichloromethane

ether

pyridine

反応条件

後処理

1. 1
   温度The resulting orange solution was cooled to 29° C.
2. 2
   その他The reaction mass exothermically
3. 3
   温度warmed to 39° C
4. 4
   温度It was further heated to 55° C. for a period of 30 minutes
5. 5
   その他whereupon much precipitate formed
6. 6
   洗浄The solution was washed with aqueous acid (5 mL of conc. HCl in 45 mL of water)
7. 7
   乾燥The organic layer was dried over MgSO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated on a rotary evaporator
10. 10
    その他Upon reduction to ˜4 mL, product crystals had formed
11. 11
    その他precipitated
12. 12
    その他The product was isolated by filtration
13. 13
    洗浄washed with ether (2×10 mL)
14. 14
    洗浄washed with water (2×50 mL)
15. 15
    その他The wet cake was dried for 30 minutes at 70° C. in vacuo

実験手順

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.

出典