2-Ethoxybenzamide → HCID 67352981, compound

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).

1. temperaturecooled by an ice bath in batches
2. customwas kept below 20° C
3. customAfter the completion of reaction
4. additionthe reactant liquid was poured into chopped ice
5. customto separate a white solid
6. additionwas added
7. customThe reaction mixture was reacted for 30 minutes under an ice bath
8. customto separate the liquid
9. washthe organic phase was washed with saturated aqueous ammonium chloride solution (100 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated to 50 mL
12. additionPetroleum ether (100 mL) was dropped
13. customto separate a white acicular crystal, 58.6 g

ORD record

ord-3445d395222949d19c832725e88c5481

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410098B2