Acetic Anhydride → 2,4-Dichloroacetanilide

HRID 2044187Notes

Reaction equation

HRID 2044187 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][C:11](OC(C)=O)=[O:12]>CC(O)=O>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:11](=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 111232,4-Dichloroaniline

Product 1

HCID 814592,4-Dichloroacetanilide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2,4-dichloroaniline (42.0 g, 260 mmol) in AcOH (40.0 mL) is added Ac2O (80 mL). The reaction mixture is warmed up to 50° C. and stirred at this temperature for 1 hour. The reaction is cooled to room temperature and poured into ice water (500 mL). A solid precipitated and the mixture is stirred for additional 1 hour at room temperature. The solid is filtered and washed with water, hexanes and air dried to give N-(2,4-dichlorophenyl)acetamide.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. customA solid precipitated
  3. stirringthe mixture is stirred for additional 1 hour at room temperature
  4. filtrationThe solid is filtered
  5. washwashed with water, hexanes and air
  6. customdried

Sources & evidence

ORD record
ord-a18c95f3ce2e4dd9a1e81cab8eec56c8
Source dataset
uspto-grants-2013_11
Patent number
US08586782B2

Reaction notes

Loading…