2-CHLORO-N-(2-METHOXYPHENYL)ACETAMIDE Chemical Properties

Melting point:

51 °C(Solv: ethanol (64-17-5))

Boiling point:

339.0±22.0 °C(Predicted)

Density 

1.264±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

12.27±0.70(Predicted)

Appearance

Light brown to brown Solid

CAS DataBase Reference

55860-22-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2924297099

2-CHLORO-N-(2-METHOXYPHENYL)ACETAMIDE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-chloro-N-(2-methoxyphenyl)acetamide from o-methoxyaniline (0.5 g, 4.05 mmol) and chloroacetyl chloride (0.387 mL, 4.87 mmol) was as follows: to a solution of acetonitrile (10.0 mL) of o-methoxyaniline under argon gas protection was added N,N-diisopropyl ethylamine (DIPEA, 1.56 mL 8.93 mmol), followed by slow dropwise addition of chloroacetyl chloride. After the dropwise addition, the reaction mixture was stirred at room temperature for 1 hour. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was concentrated and purified by column chromatography (eluent: 20% ethyl acetate/hexane) to afford the target compound 2-chloro-N-(2-methoxyphenyl)acetamide as a brown solid (0.72 g, 89.05% yield). The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 8.96 (s, 1H), 8.35 (dd, J = 1.6, 8.0 Hz, 1H), 7.14-7.10 (m, 1H), 7.02-6.97 (m, 1H), 6.94-6.91 (m, 1H), 4.21 (s, 2H), 3.93 (s, 3H).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6289 - 6304
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 24, p. 6885 - 6892
[3] Farmaco, 2002, vol. 57, # 3, p. 201 - 206
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1871 - 1879
[5] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 13, p. 3471 - 3483

2-CHLORO-N-(2-METHOXYPHENYL)ACETAMIDE(55860-22-5)Related Product Information

• 2-CHLORO-N-(2-METHOXYPHENYL)ACETAMIDE
• N1-(2,4-DIMETHOXYPHENYL)-2-CHLOROACETAMIDE
• N-(2-Methoxyphenyl)acetamide
• 2-CHLORO-N-(2,5-DIMETHOXYPHENYL)ACETAMIDE
• 2-Chloro-N-(2-methoxy-4-nitro-phenyl)-acetamide
• 2-CHLORO-N-(2-PHENOXY-PHENYL)-ACETAMIDE
• 2-CHLORO-N-(5-CHLORO-2,4-DIMETHOXYPHENYL)ACETAMIDE
• 2-CHLORO-N-(2-ETHOXYPHENYL)ACETAMIDE
• 3-(2-CHLORO-ACETYL)-3H-BENZOOXAZOL-2-ONE
• 2-CHLORO-N-(5-CHLORO-2-METHOXYPHENYL)ACETAMIDE
• 2-CHLORO-N-(2-METHOXY-5-METHYLPHENYL)ACETAMIDE
• 2-CHLORO-N-(4-CHLORO-2,5-DIMETHOXYPHENYL)ACETAMIDE
• N1-[2-(2,4-DICHLOROPHENOXY)PHENYL]-2-CHLOROACETAMIDE
• N1-[2-(4-CHLORO-3,5-DIMETHYLPHENOXY)-5-(TRIFLUOROMETHYL)PHENYL]-2,3,3-TRICHLOROACRYLAMIDE
• AURORA KA-4065
• AKOS BBS-00005468
• N1-[2-(4-CYANOPHENOXY)-5-(TRIFLUOROMETHYL)PHENYL]-2-CHLOROACETAMIDE
• N1-[2-(4-CHLORO-3,5-DIMETHYLPHENOXY)-5-(TRIFLUOROMETHYL)PHENYL]-2-CHLOROACETAMIDE