Dichloroacetyl chloride → 2,2-dichloro-N-cyclopropylacetamide

HRID 258491Notes

Reaction equation

HRID 258491 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:12][CH:13]([Cl:17])[C:14](Cl)=[O:15]>C1C=CC=CC=1>[CH:1]1([NH:4][C:14](=[O:15])[CH:13]([Cl:17])[Cl:12])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 69828Cyclopropylamine

Product 1

HCID 3351372,2-dichloro-N-cyclopropylacetamideYield 82%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of cyclopropylamine (28.6 g, 0.5 mol) and 50 ml of triethylamine in 200 ml of anhydrous benzene was added dropwise with stirring and ice-bath cooling dichloroacetyl chloride (73.7 g, 0.5 mol). The solution was stirred 2 hr at room temperature. The benzene solution was washed successively with 10% HCl, H2O and saturated NaCl solution and dried over anhydrous MgSO4. The solvent was distilled affording 68.3 g (82%) of white crystalline product, m.p. 125-71/4. Recrystallization from ethanol-benzene yielded purified product; m.p. 130°-2°.

Workup

  1. stirringThe solution was stirred 2 hr at room temperature
  2. washThe benzene solution was washed successively with 10% HCl, H2O and saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. distillationThe solvent was distilled

Sources & evidence

ORD record
ord-f7694e60287b4aab8bd4ecb55cf87f7f
Source dataset
uspto-grants-1977_07
Patent number
US04033756

Reaction notes

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