4-Methoxybenzenesulfonyl chloride → N1-(cyclohexyloxy)-4-methoxy-1-benzenesulfonamide

2-(cyclohexyloxy)-1H-isoindole-1,3(2H)-dione (11.8 mmol, 2.89 g) was combined with hydrazine (13.0 mmol, 0.41 mL) in anhydrous THF (20 mL) under nitrogen. The reaction immediately formed a white suspension and was allowed to stir at room temperature for 18 hours. The suspension was filtered directly into a flask containing 4-methoxybenzenesulfonyl chloride (10.6 mmol, 2.20 g) and diisopropylethylamine (14.2 mmol, 2.47 mL) was added. After stirring at room temperature for 24 hours, the reaction was concentrated to a yellow solid 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 yellow solid and purified by silica gel chromatography (1:1 hexanes/ethyl acetate) providing 2.53 g (83%) of a white solid. Rf: 0.2 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.86 (2H,d), 7.00 (2H,d), 6.67 (1H,s), 3.98-3.95 (1H,m), 3.88 (3H,s), 2.00-1.94 (2H,m), 1.75-1.55 (2H,m), 1.35-1.17 (6H,m).

1. customThe reaction
2. customimmediately formed a white suspension
3. filtrationThe suspension was filtered directly into a flask
4. additionwas added
5. stirringAfter stirring at room temperature for 24 hours
6. concentrationthe reaction was concentrated to a yellow solid
7. custompartitioned between ethyl acetate and 1N HCl
8. customThe organic layer was separated
9. washwashed with a saturated aqueous solution of sodium bicarbonate, and brine
10. dry with materialdried over magnesium sulfate
11. concentrationThe product was concentrated to a yellow solid
12. custompurified by silica gel chromatography (1:1 hexanes/ethyl acetate)

ORD record

ord-bb32ffc2359643ceba469b0ed502d6c0

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613743B2