تفاعل #2045128

معادلة التفاعل

Orthoethoxybenzamide

chlorosulfonic acid

thionyl chloride

N-ethylpiperazine

→

final product

المردود 86.0%

2-ethoxy-5-(4-ethylpiperazin-1-yl-sulfonyl)benzamide

المردود 86.0%

المذيبات

Water

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled by an ice bath in batches
2. 2
   أخرىwas kept below 20° C
3. 3
   أخرىAfter the completion of reaction
4. 4
   workup.ADDITIONthe reactant liquid was poured into chopped ice
5. 5
   أخرىto separate a white solid
6. 6
   workup.ADDITIONwas added
7. 7
   أخرىThe reaction mixture was reacted for 30 minutes under an ice bath
8. 8
   أخرىto separate the liquid
9. 9
   غسيلthe organic phase was washed with saturated aqueous ammonium chloride solution (100 mL)
10. 10
    تجفيفdried over anhydrous sodium sulfate
11. 11
    تركيزconcentrated to 50 mL
12. 12
    workup.ADDITIONPetroleum ether (100 mL) was dropped
13. 13
    أخرىto separate a white acicular crystal, 58.6 g

الإجراء التجريبي

Orthoethoxybenzamide (33.0 g, 0.20 mol) was added into a mixture of chlorosulfonic acid (60 mL) and thionyl chloride (20 mL) cooled by an ice bath in batches, and the temperature of the reaction system was kept below 20° C. After the completion of reaction identified by TLC, the reactant liquid was poured into chopped ice to separate a white solid. The product was extracted out with dichloromethane (200 mL), and N-ethylpiperazine (45.6 g, 0.40 mol) was added therein under an ice bath. The reaction mixture was reacted for 30 minutes under an ice bath, and then stirred for 1 hour at room temperature. Water (10 mL) was added therein to separate the liquid, and the organic phase was washed with saturated aqueous ammonium chloride solution (100 mL), dried over anhydrous sodium sulfate, and concentrated to 50 mL. Petroleum ether (100 mL) was dropped therein to separate a white acicular crystal, 58.6 g, and the final product was obtained by vacuum filtration with a yield of 86%. 1H NMR (CDCl3, 300 MHz) δ: 1.01 (3H, t), 1.56 (3H, t), 2.38 (2H, q), 2.50 (4H, t), 3.03 (4H, t), 4.28 (2H, q), 6.14 (1H, s), 7.06 (1H, d), 7.67 (1H, s), 7.82 (1H, dd), 8.58 (1H, d).

المصدر