반응 #57438

반응 방정식

2-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

hydrazine

4-methoxybenzenesulfonyl chloride

diisopropylethylamine

→

yellow solid

수율 89.7%

N1-(cyclohexylmethoxy)-4-methoxy-1-benzenesulfonamide

수율 89.7%

용매

THF

반응 조건

후처리

1. 1
   기타The reaction
2. 2
   기타immediately formed a white suspension
3. 3
   여과The suspension was filtered directly into a flask
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGAfter stirring at room temperature for 18 hours
6. 6
   농축the reaction was concentrated to a solid residue
7. 7
   기타partitioned between ethyl acetate and 1N HCl
8. 8
   기타The organic layer was separated
9. 9
   세척washed with a saturated aqueous solution of sodium bicarbonate, and brine
10. 10
    건조dried over magnesium sulfate
11. 11
    농축The product was concentrated to a solid
12. 12
    기타purified by silica gel chromatography (2:1 hexanes/ethyl acetate)

실험 절차

2-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione (11.8 mmol, 3.05 g) was combined with hydrazine (12.9 mmol, 0.41 mL) in anhydrous THF (25 mL) under nitrogen. The reaction immediately formed a white suspension and was allowed to stir at room temperature for 48 hours. The suspension was filtered directly into a flask containing 4-methoxybenzenesulfonyl chloride (9.5 mmol, 1.97 g) and diisopropylethylamine (11.6 mmol, 2.03 mL) was added. After stirring at room temperature for 18 hours, the reaction was concentrated to a solid residue and partitioned between ethyl acetate and 1N HCl. The organic layer was separated and washed with a saturated aqueous solution of sodium bicarbonate, and brine, and dried over magnesium sulfate. The product was concentrated to a solid and purified by silica gel chromatography (2:1 hexanes/ethyl acetate) providing 2.55 g (80%) of a yellow solid. H1-NMR (CDCl3): δ 7.81 (2H,d), 6.97 (2H,d), 6.78 (1H,s), 3.85 (3H,s), 3.75 (2H,d), 1.65-1.55 (6H,m), 1.25-1.07 (3H,m), 0.93-0.85 (2H,m).

출처