Chloroacetyl chloride → HCID 53886132, compound

HRID 745701Notes

Reaction equation

HRID 745701 reaction equation
[CH:1](=[N:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[CH:2]=[CH:3][CH3:4].[Cl:14][CH2:15][C:16](Cl)=[O:17].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:1]([N:5]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[C:16](=[O:17])[CH2:15][Cl:14])=[CH:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 54221942HCID 54221942, compound

Product 1

HCID 53886132HCID 53886132, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

17.3 g (0.1 mol) of N-but-2-enylidene-2,6-dimethylaniline were added dropwise to a solution of 11.3 g (0.1 mol) of chloroacetyl chloride in 10 ml of toluene at 20° C. The mixture was further stirred at 20° C. for 1 hour and 10.1 g (0.1 mol) of triethylamine were then added dropwise. The mixture was further stirred at 20° C. for 1 hour and the precipitate which separated off was filtered off under suction. The filtrate was washed with dilute aqueous bicarbonate solution and then with water, and was subsequently concentrated in vacuo. The residue was recrystallized from hexane. 12.4 g (49.7% of theory) of N-(1,3-butadienyl)-N-(2,6-dimethylphenyl)chloroacetamide were obtained in the form of colorless crystals of melting point 88° C.

Workup

  1. stirringThe mixture was further stirred at 20° C. for 1 hour
  2. customthe precipitate which separated off
  3. filtrationwas filtered off under suction
  4. washThe filtrate was washed with dilute aqueous bicarbonate solution
  5. concentrationwith water, and was subsequently concentrated in vacuo
  6. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-efbf3d277a7a4ae6970043b9fe427547
Source dataset
uspto-grants-1986_07
Patent number
US04599448

Reaction notes

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