3,4-Dichloroaniline → 3,4-Dichloroanilinoacetonitrile

HRID 67085Notes

Reaction equation

HRID 67085 reaction equation
Cl[CH2:2][C:3]#[N:4].[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[Cl:13])[NH2:9]>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[Cl:13])[NH:9][CH2:2][C:3]#[N:4]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 7856Chloroacetonitrile

Product 1

HCID 128325593,4-DichloroanilinoacetonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetonitrile (45.3 grams (g)) and 97.2 g of 3,4-dichloroaniline were heated with stirring in a 250 milliliter (ml) round-bottomed three-necked flask at about 120°-125° C. for 2 hours. The reaction mixture was cooled, then diluted with methylene chloride and then filtered to remove the 3,4-dichloroaniline hydrochloride (52.4 g) which had formed. The filtrate was concentrated to dryness under vacuum, leaving a black gummy residue that crystallized on cooling. The residue was put in solution in hot toluene, the solution was then cooled and filtered, which gave 38.3 g of crude product. Recrystallization from cyclohexane gave 36.2 g of purified 3,4-dichloroanilinoacetonitrile as pink crystals, having a melting point (m.p.) of 95°-97° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customto remove the 3,4-dichloroaniline hydrochloride (52.4 g) which
  4. customhad formed
  5. concentrationThe filtrate was concentrated to dryness under vacuum
  6. customleaving a black gummy residue that
  7. customcrystallized
  8. temperatureon cooling
  9. temperaturethe solution was then cooled
  10. filtrationfiltered
  11. customwhich gave 38.3 g of crude product
  12. customRecrystallization from cyclohexane

Sources & evidence

ORD record
ord-94afeb6010124009afd4d36b20b5201a
Source dataset
uspto-grants-1982_08
Patent number
US04344958

Reaction notes

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