3,4-Dichloroaniline → N-(3,4-Dichlorophenyl)prop-2-enamide

HRID 1384465

Reaction equation

HRID 1384465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].C(N(CC)CC)C.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:17](=[O:20])[CH:18]=[CH2:19])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 13411358N-(3,4-Dichlorophenyl)prop-2-enamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3,4-dichloroaniline (3.6 g, 22.3 mmol) and 4.2 mL (30.2 mmol) of triethylamine in 20 mL of anhydrous methylene chloride was cooled to 0° C. under a nitrogen atmosphere and treated with acryloyl chloride (2.1 g, 23.2 mmol). The ice bath was removed and the mixture was stirred at room temperature for 1 hour after which time it was diluted with 120 mL of methylene chloride and washed with water and saturated aqueous sodium chloride (NaCl). After drying with calcium sulfate (CaSO4), the solvent was removed in vacuo to give a yellow solid, 4.84 g.

Workup

  1. customThe ice bath was removed
  2. additionwas diluted with 120 mL of methylene chloride
  3. washwashed with water and saturated aqueous sodium chloride (NaCl)
  4. dry with materialAfter drying with calcium sulfate (CaSO4)
  5. customthe solvent was removed in vacuo
  6. customto give a yellow solid, 4.84 g

Sources & evidence

ORD record
ord-90163b68f8e64eb88eae794c08d34b46
Source dataset
uspto-grants-2001_07
Patent number
US06258953B1

Linked notes

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