4-Methylmorpholine → 2-Amino-4,6-dichlorobenzamide

To a solution of 2-amino-4,6-dichloro-benzoic acid (4.12 g, 20.0 mmol) in THF (120 mL) were added EDCl (4.22 g, 22.0 mmol), HOBt (2.70 g, 20.0 mmol) and N-methylmorpholine (2.22 g, 22.0 mmol). The reaction mixture was stirred at room temperature for 20 minutes, then 50% (v/v) aqueous NH4OH solution (2.8 mL, 40.0 mmol) was added. The mixture was stirred for 20 hours at room temperature. The solvent was evaporated, the residue was taken in ethyl acetate (200 mL), and water (200 mL) was added. The organic phase was separated; the aqueous phase was extracted with ethyl acetate (200 mL). The combined organic phase was washed with water (100 mL), then brine (100 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated and dried under vacuum to give 2-amino-4,6-dichloro-benzamide as an off-white solid. Yield: 3.83 g (93%).

1. stirringThe mixture was stirred for 20 hours at room temperature
2. customThe solvent was evaporated
3. additionwater (200 mL) was added
4. customThe organic phase was separated
5. extractionthe aqueous phase was extracted with ethyl acetate (200 mL)
6. washThe combined organic phase was washed with water (100 mL)
7. dry with materialbrine (100 mL), and dried over anhydrous sodium sulfate
8. customThe solvent was evaporated
9. customdried under vacuum

ORDレコード

ord-0cfc8e414aec4cd38148cb4792e3b013

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09238640B2