Dichloroacetyl chloride → HCID 13309297, compound

HRID 1680108Notes

Reaction equation

HRID 1680108 reaction equation
[CH:1]([NH:4][CH2:5][C:6]#[CH:7])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:15][CH:16]([Cl:20])[C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[CH:1]([N:4]([CH2:5][C:6]#[CH:7])[C:17](=[O:18])[CH:16]([Cl:20])[Cl:15])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 243521N-(Propan-2-yl)prop-2-yn-1-amine

Product 1

HCID 13309297HCID 13309297, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

118 g of isopropylpropargylamine and 123 g of triethylamine are dissolved in 670 ml of toluene. While cooling and at room temperature, a solution of 180 g of dichloroacetyl chloride in 450 ml of toluene is dripped into this solution. The mixture is allowed to react for 1 hour before being filtered, and the filtrate is washed with water. The residue remaining after removal of the solvent is washed with petroleum ether. There is obtained 214 g (84% of theory) of N-isopropyl-N-propargyldichloroacetamide; b.p. (0.013 mbar): 80°-82° C.; m.p.: 58°-59° C.

Workup

  1. customto react for 1 hour
  2. filtrationbefore being filtered
  3. washthe filtrate is washed with water
  4. customafter removal of the solvent
  5. washis washed with petroleum ether

Sources & evidence

ORD record
ord-6e337ad1443b426797f781b212427801
Source dataset
uspto-grants-1981_06
Patent number
US04272282

Reaction notes

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