Acetyl chloride → Acetanilide, 2',4',5'-trichloro-

HRID 1577620Notes

Reaction equation

HRID 1577620 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:7]=1[NH2:8]>ClCCl>[CH3:2][C:1]([NH:8][C:7]1[C:6]([Cl:5])=[CH:12][C:11]([Cl:13])=[C:10]([Cl:14])[CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 124872,4,5-Trichloroaniline

Product 1

HCID 90217Acetanilide, 2',4',5'-trichloro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Acetyl chloride (2.13 mls; 0.03 mole) is added dropwise to a suspension of 2,4,5-trichloroaniline (4.91 g; 0.025 mole) and powdered 3A molecular sieves (7.4 g) in dichloromethane (25 mls), at room temperature, under a nitrogen atmosphere. When addition is completed, the mixture is heated to 50° C. for 1.5 hours and then cooled to room temperature. The 3A sieves are separated by filtration and washed with dichloromethane. All dichloromethane solutions are combined and evaporated to obtain 4.1 grams (69% of theoretical) of the solid product; m.p. 188°-190° C. after recrystallized from toluene.

Workup

  1. customat room temperature
  2. additionWhen addition
  3. temperaturecooled to room temperature
  4. customThe 3A sieves are separated by filtration
  5. washwashed with dichloromethane
  6. customevaporated
  7. customto obtain 4.1 grams (69% of theoretical) of the solid product
  8. customm.p. 188°-190° C. after recrystallized from toluene

Sources & evidence

ORD record
ord-55fa5f57c1224c8aa63b76b6d398bdcc
Source dataset
uspto-grants-1981_09
Patent number
US04288592

Reaction notes

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