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-325f4ba7e8ab4d0b84a86af8116fb064

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE043833E1