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

HRID 542604

Reaction equation

HRID 542604 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 89%

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 lN 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 of lN hydrochloric acid
  4. dry with materialThe resulting toluene solution was dried
  5. concentrationit was concentrated in vacuo

Sources & evidence

ORD record
ord-09e10b9cb40049dabfbb21aac122792a
Source dataset
uspto-grants-1987_04
Patent number
US04658037

Linked notes

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