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

HRID 4469

Reaction equation

HRID 4469 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

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 97083-Chloro-4-fluoroaniline

Product 1

HCID 7358492-chloro-N-(3-chloro-4-fluorophenyl)acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 130 ml. of toluene was added, with stirring, 24.0 g. (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. temperatureThe resulting solution was cooled to ca 0° C.
  2. stirringThe reaction mixture was stirred at room temperature for 5 hours
  3. extractionit was extracted twice with 100 ml
  4. dry with materialThe resulting toluene solution was dried
  5. concentrationit was concentrated in vacuo
  6. customto give 32.6 g

Sources & evidence

ORD record
ord-67d46a104ad240b9a00c308bf07eb4cb
Source dataset
uspto-grants-1988_02
Patent number
US04725616

Linked notes

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