Methylamine → Benzamide, 4-chloro-N-methyl-

To a 0° C. solution of the 4-chlorobenzoyl chloride (4.50 g) in dichloromethane (10 mL) was added an 8M solution of methylamine in ethanol dropwise. The solution was stirred for 16 h and then evaporated to dryness. The residue was diluted with saturated sodium bicarbonate solution (10 mL) and extracted three times with ethyl acetate (3×20 mL), the organics washed with brine (10 mL), dried (MgSO4) and concentrated in vacuo to afford the sub-title compound as a white solid (4.33 g; 97%): 1H NMR (400 MHz, CDCl3) δ 3.00 (3H, s), 7.40 (1H, brs) 7.40 (1H, d), 7.70 (1H, d)

1. customevaporated to dryness
2. additionThe residue was diluted with saturated sodium bicarbonate solution (10 mL)
3. extractionextracted three times with ethyl acetate (3×20 mL)
4. washthe organics washed with brine (10 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-0a11c896cb52438eaca7157c4aa9bc3c

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612091B2