2-Chloro-N-(2-methoxyphenyl)acetamide

To a solution of compound A (0.5 g, 4.05 mmoles) in ACN (10.0 mL) was added DIPEA (1.56 mL, 8.93 mmoles), followed by dropwise addition of compound B (0.387 mL, 4.87mmoles) under argon atmosphere. After the addition was complete the reaction was stirred at rt for 1 hour. The completion of the reaction was monitored byTLC. The reaction mixture was concentrated, purified by column chromatography(20 percent EtOAc:Hexanes) to isolate the required compound as brown solid (0.72 g, 89.05percent). The procedure described in Example 22A was followed, substituting 2-methoxyaniline (Acros) for 3, 4, 5-trimethoxyaniline, to provide the title compound (83percent yield) as a brown solid. 1H NMR (300 MHz, DMSO-d6) ' 3.85 (s, 3H), 4.38 (s, 2H), 6.92 (m, 1H), 7.08 (m, 2H), 7.91 (d, 1H, J=7.8 Hz), 9.48 (br s, 1H); MS (DCI/NH3) m/e 200 (M+H)+.Chloroacetyl chloride (11.3 g, 100 mmol) was slowly added to 2-methoxyaniline (12.3 g, 100 mmol) in dioxan (100 mL), then the mixture was heated under reflux for 1 h. General procedure: Chloroacetyl chloride (0.06 mol) was added dropwise toa mixture of the appropriate amine (0.05 mol) and K2CO3(0.06 mol) in acetone (50 ml) at room temperature. Thereaction mass was refluxed for 4–8 h, and then progress of reaction was monitored by TLC using ethyl acetate–hexane(8:2) solvent system as eluent. Then the reaction mixture was cooled and poured into 100 ml of ice water. The resulting white precipitates were filtered off and dried under the vacuum condition and purified by recrystallization from alcohol. Similarly, other compounds (5a–5j) were prepared by using various substituted amines.

Molecular Weight:199.63
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:199.0400063
Monoisotopic Mass:199.0400063
Topological Polar Surface Area:38.3
Heavy Atom Count:13
Complexity:175
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes