Dichloroacetyl chloride → Acetamide, 2,2-dichloro-N,N-bis(1-methylethyl)-

HRID 1706590Notes

Reaction equation

HRID 1706590 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:15][CH:16]([Cl:20])[C:17](Cl)=[O:18]>C1C=CC=CC=1>[CH:1]([N:4]([CH:5]([CH3:7])[CH3:6])[C:17](=[O:18])[CH:16]([Cl:20])[Cl:15])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 7912DiisopropylamineHCID 8471Triethylamine

Product 1

HCID 79228Acetamide, 2,2-dichloro-N,N-bis(1-methylethyl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of diisopropylamine (6.8 g) (0.068 mol) and 6.8 g. of triethylamine in 100 ml of anhydrous benzene was added dropwise at 15° C. with stirring and ice-bath cooling, dichloroacetyl chloride (10.0 g, 0.068 mol). The solution was stirred overnight at room temperature. The benzene solution was washed successively with 10% HCl, H2O sodium hydroxide and saturated NaCl solution and was dried over anhydrous MgSO4. The solvent was distilled off, yielding 4.9 g. of liquid product, which infrared absorption spectra indicated to be substantially pure. No further purification was considered to be necessary for the purpose of this invention.

Workup

  1. temperatureice-bath cooling
  2. stirringThe solution was stirred overnight at room temperature
  3. washThe benzene solution was washed successively with 10% HCl, H2O sodium hydroxide and saturated NaCl solution
  4. dry with materialwas dried over anhydrous MgSO4
  5. distillationThe solvent was distilled off
  6. customyielding 4.9 g
  7. customabsorption spectra
  8. customNo further purification

Sources & evidence

ORD record
ord-8bb65c6e7091410cb90035247171b927
Source dataset
uspto-grants-1980_06
Patent number
US04208203

Reaction notes

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