반응 #57430

반응 방정식

N,N-diisopropylethylamine

hydrazine

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

4-methoxybenzenesulphonyl chloride

→

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

수율 79.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   여과the resulting slurry was filtered
2. 2
   세척washed with approximately 15 mL of anhydrous tetrahydrofuran
3. 3
   workup.STIRRINGAfter stirring at ambient temperature for approximately 18 hours
4. 4
   기타the reaction mixture was evaporated in vacuo to a residue
5. 5
   기타partitioned between ethyl acetate and 1N hydrochloric acid
6. 6
   기타The layers were separated
7. 7
   추출the organic phase was extracted again with ethyl acetate
8. 8
   세척The combined organic layers were washed with 5% w/v potassium carbonate and brine
9. 9
   건조dried over anhydrous magnesium sulfate
10. 10
    여과filtered
11. 11
    기타evaporated in vacuo to a residue
12. 12
    기타The crude material was purified on flash grade silica gel eluting with 15:85 ethyl acetate
13. 13
    workup.ADDITIONFractions containing the product
14. 14
    기타evaporated in vacuo
15. 15
    기타dried under high vacuum

실험 절차

A mixture of 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione (3.00 g, 12.99 mmol) in anhydrous tetrahydrofuran (15 mL) at ambient temperature under an Argon atmosphere was treated with anhydrous hydrazine (0.448 mL, 14.29 mmol). After stirring vigorously for 1.5 hours, the resulting slurry was filtered and washed with approximately 15 mL of anhydrous tetrahydrofuran. The filtrate was combined with 4-methoxybenzenesulphonyl chloride (2.95 g, 14.29 mmol) and N,N-diisopropylethylamine (2.72 mL, 15.6 mmol). After stirring at ambient temperature for approximately 18 hours, 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 organic phase 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 15:85 ethyl acetate:hexane. Fractions containing the product were combined, evaporated in vacuo, and dried under high vacuum to provide N1-(cyclopentyloxy)-4-methoxy-1-benzenesulfonamide (2.771 g, 79%) as an oil. H1-NMR (chloroform-D3): 1.61 (m, 8H), 3.87 (s, 3H), 4.57 (m, 1H), 6.67 (s, 1H), 6.99 (m, 2H), 7.83 (m, 2H). MS(ESI): 294 (M+Na).

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