Pyridine → 2-chloro-N-(3-chloro-4-fluorophenyl)acetamide

HRID 568799

Reaction equation

HRID 568799 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].N1C=CC=CC=1.[Cl:16][CH2:17][C:18](Cl)=[O:19]>C1(C)C=CC=CC=1>[Cl:16][CH2:17][C:18]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([F:9])=[C:2]([Cl:1])[CH:3]=1)=[O:19]

Participants

5

Conditions

Temperature
0 °C

Procedure

To 130 ml of toluene was added, with stirring, 24.0 g (0.0.165 mole) of 3-chloro-4-fluoroaniline and 13.5 ml (0.166 mole) of pyridine. The resulting solution was cooled to ca. 0° C. and 13.2 ml (0.166 mole) of 2-chloroacetyl chloride was added. The reaction mixture was stirred at room temperature for 5 hours and then it was extracted twice with 100 ml of 1N hydrochloric acid, followed by 100 ml of saturated sodium chloride solution. The resulting toluene solution was dried using magnesium sulfate, and then it was concentrated in vacuo to give 32.6 g (88% yield) of N-(2-chloroacetyl)-3-chloro-4-fluoroaniline.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 hours
  2. extractionit was extracted twice with 100 ml of 1N hydrochloric acid
  3. dry with materialThe resulting toluene solution was dried
  4. concentrationit was concentrated in vacuo

Sources & evidence

ORD record
ord-fbe8e39439da4f3e96f607815950e384
Source dataset
uspto-grants-1988_03
Patent number
US04730004

Linked notes

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