반응 #57475

반응 방정식

4-tetrahydropyranoxyhydroxylamine

diisopropylethylamine

Hydrazine

4-nitrobenzenesulfonylchloride

→

white crystals

수율 36.0%

4-nitro-N-(tetrahydro-2H-pyran-4-yloxy)benzenesulfonamide

수율 36.0%

용매

THF

ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred for an additional 24 hours
2. 2
   세척washed in brine
3. 3
   여과filtered
4. 4
   기타to remove insoluble solids
5. 5
   농축concentrated
6. 6
   기타The crude was purified by crystallization from hot ethyl acetate

실험 절차

4-tetrahydropyranoxyhydroxylamine (33.2 mmol, 3.77 g) and 4-nitrobenzenesulfonylchloride (38.6 mmol, 8.56 g) were combined in anhydrous THF (100 mL) with diisopropylethylamine (69.3 mmol, 11.2 mL). The reaction was stirred at room temperature for 48 hours. Hydrazine (2 mL) was injected to the stirring solution to break-up the bisarylsulfonamide dimer biproduct. The reaction was stirred for an additional 24 hours. The reaction was diluted in ethyl acetate, washed in brine, filtered to remove insoluble solids and concentrated. The crude was purified by crystallization from hot ethyl acetate to provide 3.5 g (36%) of white crystals. Rf=0.3 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 8.42 (2H,d), 8.13 (2H,d), 6.93 (1H,s), 4.27 (1H,m), 3.91 (2H,m), 3.45 (2H,m), 2.02 (2H,m), 1.61 (2H,m).

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