Acetic Acid → 2-Amino-5-Chloro-N,3-Dimethylbenzamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[NH:10]C(=O)[O:8][C:7](=O)[C:6]=2[CH:13]=1.C(OCC)(=O)C.C(O)(=O)C.[CH3:25][NH2:26]>O>[NH2:10][C:5]1[C:4]([CH3:14])=[CH:3][C:2]([Cl:1])=[CH:13][C:6]=1[C:7]([NH:26][CH3:25])=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
A 250-mL flask equipped with thermometer and nitrogen bubbler was charged with 6-chloro-8-methyl-2H-3,1-benzoxazine-2,4(1H)-dione (21.0 g, 0.099 mol) (i.e. the product of Example 1), ethyl acetate (100 mL), and acetic acid (12.6 g, 0.21 mol). The mixture was stirred at 22° C., and anhydrous methylamine (4.3 g, 0.14 mol) was added below the surface of the mixture in portions over 45 minutes while maintaining the temperature at 22-41° C. The mixture was held for 2 h at 40° C., then water (150 mL) was added, and the ethyl acetate was removed by distillation. When the pot temperature reached 83° C., the solution was seeded, and the product slurry was cooled over about 2 h to 10° C. The solid was collected by filtration, washed with water and dried to afford the title compound as a white crystalline solid (18.38 g, >97.4 wt. % purity by HPLC, 94% yield) melting at 143-145° C.
Workup
- customA 250-mL flask equipped with thermometer and nitrogen bubbler
- temperaturewhile maintaining the temperature at 22-41° C
- customthe ethyl acetate was removed by distillation
- customreached 83° C.
- temperaturethe product slurry was cooled over about 2 h to 10° C
- filtrationThe solid was collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-f99c68e3cd58494ea85d2348797c8862
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153844B2
Reaction notes
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