تفاعل #816440

معادلة التفاعل

N-(2-methoxyethyl)-1-phenylmethanesulfonamide

diethyl oxalate

Potassium tert-butoxide

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title compound

المردود 6.1%

4-Hydroxy-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

المردود 6.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىwas removed
2. 2
   workup.ADDITIONHCl (2M, 45 mL) was added to the mixture
3. 3
   استخلاصthe acidic solution was extracted 3 times with DCM
4. 4
   غسيلThe combined organic layer was washed 4 times with water
5. 5
   أخرىdried through a phase separator
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue was purified by preparative HPLC [0.1M N OAc/MeCN, gradient A:B (9:1 to 1:9)]

الإجراء التجريبي

A solution of N-(2-methoxyethyl)-1-phenylmethanesulfonamide (3.5 g, 14.5 mmol) and diethyl oxalate (2.33 g, 16.0 mmol) in dry DMF was cooled in an ice-bath. Potassium tert-butoxide (2.17 g, 18.4 mmol) was added and after 5 min the ice-bath was removed and the reaction was stirred at rt for 22 h. HCl (2M, 45 mL) was added to the mixture and the acidic solution was extracted 3 times with DCM. The combined organic layer was washed 4 times with water, dried through a phase separator and evaporated. The residue was purified by preparative HPLC [0.1M N OAc/MeCN, gradient A:B (9:1 to 1:9)] to give the title compound (0.250 g, 6%) as a solid; 1H NMR (500 MHz, CD3OD): δ 7.90-7.94 (m, 2H), 7.28-7.33 (m, 2H), 7.10-7.15 (m, 1H), 3.79 (t, 2H), 3.68 (t, 2H), 3.34 (s, 3H); Mass Spectrum: M−H+ 282.

المصدر