반응 #57428

반응 방정식

4-methoxybenzenesulphonyl chloride

N,N-diisopropylethylamine

hydrazine

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

→

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

수율 69.0%

용매

dichloromethane

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.WAITAfter an additional 2 hours at ambient temperature
2. 2
   기타the reaction mixture was evaporated in vacuo to a residue
3. 3
   기타partitioned between ethyl acetate and 1N hydrochloric acid
4. 4
   기타The layers were separated
5. 5
   추출the aqueous layer was extracted again with ethyl acetate
6. 6
   세척The combined organic layers were washed with 5% w/v potassium carbonate and brine
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과filtered
9. 9
   기타evaporated in vacuo to a residue
10. 10
    기타The crude material was purified on Flash grade silica gel eluting with 30% ethyl acetate in hexane
11. 11
    workup.ADDITIONFractions containing the product
12. 12
    기타evaporated in vacuo
13. 13
    기타dried under high vacuum

실험 절차

A vigorously stirred solution of 2-isopropoxy-1H-isoindole-1,3(2H)-dione [2.50 g, 12.2 mmol, Synth. Comm., 22(10), 1427-1432 (1992)] in 35 mL of tetrahydrofuran under an Argon atmosphere at ambient temperature was treated with anhydrous hydrazine (0.421 mL, 13.41 mmol). After 1.5 hours, 4-methoxybenzenesulphonyl chloride (3.024 g, 14.63 mmol), dichloromethane (20 mL) and N,N-diisopropylethylamine (6.38 mL, 36.6 mmol) was added with continued stirring. After an additional 2 hours at ambient temperature, the reaction mixture was evaporated in vacuo to a residue and partitioned between ethyl acetate and 1N hydrochloric acid. The layers were separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layers were washed with 5% w/v potassium carbonate and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue. The crude material was purified on Flash grade silica gel eluting with 30% ethyl acetate in hexane. Fractions containing the product were combined, evaporated in vacuo, and dried under high vacuum to provide N1-(isopropoxy)-4-methoxy-1-benzenesulfonamide (2.061 g, 69%) as a white solid. H1-NMR (chloroform-D3): 1.22 (d, 6H), 3.92 (s, 3H), 4.27 (m, 1H), 6.70 (s, 1H), 7.05 (d, 2H), 7.90 (d, 2H). MS(ESI): 268 (M+Na).

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