Dimethylamine → HCID 18870829, compound

A mixture of chloroacetanilide (10.0 g, 59 mmol) in dimethylamine, 40% wt in water (100 ml) was refluxed for 4 hours. The cooled reaction mixture was partitioned between dichloromethane (100 ml) and 1M NaOH aqueous solution (100 ml). The aqueous layer was extracted twice more with dichloromethane (2×100 ml), the combined organic layers were concentrated in vacuo to a volume of approximately 100 ml and washed with water (2×100 ml) in order to remove the remaining dimethylamine. The organic layer was collected, dried over sodium sulfate and the solvent evaporated in vacuo to provide 10.2 g (97% yield) of the pure dimethylaminoacetanilide. 1H NMR (CDCl3, 200 MHz) δ: 9.1 (br. s, NH, 1H), 7.6-7.0 (m, Ar, 5H) 3.1 (s, CH2, 2H), 2.4 (s CH3, 6H).

1. temperaturewas refluxed for 4 hours
2. customThe cooled reaction mixture
3. customwas partitioned between dichloromethane (100 ml) and 1M NaOH aqueous solution (100 ml)
4. extractionThe aqueous layer was extracted twice more with dichloromethane (2×100 ml)
5. concentrationthe combined organic layers were concentrated in vacuo to a volume of approximately 100 ml
6. washwashed with water (2×100 ml) in order
7. customto remove the remaining dimethylamine
8. customThe organic layer was collected
9. dry with materialdried over sodium sulfate
10. customthe solvent evaporated in vacuo

ORD record

ord-9070bf5347ad49348dfdf59f6880ab75

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362197B1