Aniline → Chloroacetanilide

A solution of aniline (9.31 g, 100 mmol) and triethylamine (15.2 g, 150 mmol) in THF (150 mL) is cooled to −40° C. before chloroacetic acid chloride (11.3 g, 100 mmol) is slowly added in portions such that the temperature does not rise above 0° C. After completion of the addition, the brown suspension is stirred at rt for 1 h. The dark purple mixture is poured onto water (300 mL) and extracted twice with EA (300 mL). The organic extracts are washed with sat. aq. NaHCO3, 0.5 N aq. HCl, followed by water, and evaporated. The brown residue is suspended in diethyl ether, filtered off, washed with additional diethyl ether and dried under high vacuum to give 2-chloro-N-phenyl-acetamide. LC-MS: tR=0.75 min, [M+1]+=170, 1H NMR (CDCl3): δ 8.22 (s br, 1H), 7.56-7.51 (m, 2H), 7.40-7.24 (m, 2H), 7.20-7.14 (m, 1H), 4.20 (s, 2H).

1. additionis slowly added in portions such that the temperature
2. customdoes not rise above 0° C
3. additionAfter completion of the addition
4. additionThe dark purple mixture is poured onto water (300 mL)
5. extractionextracted twice with EA (300 mL)
6. washThe organic extracts are washed with sat. aq. NaHCO3, 0.5 N aq. HCl
7. customevaporated
8. filtrationfiltered off
9. washwashed with additional diethyl ether
10. customdried under high vacuum

ORD record

ord-56994b97fd3d4d8780cb7480791f0e2f

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524752B2