Dimethylamine → 2-Amino-5-bromo-N,N-dimethylbenzamide

Temperature

60 °C

Into a 350 ml round bottomed pressure tube were added 5-bromoisatoic anhydride (15.0 g, 62.0 mmol) and 2 M dimethylamine in tetrahydrofuran (90 ml, 180 mmol). The vial was sealed and heated in an oil bath at 60° C. for 1 hour, then the mixture was concentrated to dryness. The residue was dissolved in dichloromethane (100 ml). The organic layer washed with saturated, aqueous sodium bicarbonate solution (25 ml), washed with water (25 ml), dried over sodium sulfate, filtered, and concentrated to obtain a yellow powder. The powder was re-crystallized from ether to obtain 11.8 g (78.6%) of 2-amino-5-bromo-N,N-dimethyl-benzamide. 1H-NMR (250 MHz, CDCl3) δ 7.20 (dd, J=8.5, 2.5 Hz, 1H), 7.10 (d, J=2.5 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 5.34 (s, 2H), 2.91 (s, 6H); MS m/z 243.1, 245.1 (M+H+).

1. customThe vial was sealed
2. concentrationthe mixture was concentrated to dryness
3. dissolutionThe residue was dissolved in dichloromethane (100 ml)
4. washThe organic layer washed with saturated, aqueous sodium bicarbonate solution (25 ml)
5. washwashed with water (25 ml)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto obtain a yellow powder
10. customThe powder was re-crystallized from ether

ORD record

ord-a35b1eb4f113492c92a2f701def2ddad

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709645B2