Dichloroacetyl chloride → HCID 54004955, compound

HRID 330459Notes

Reaction equation

HRID 330459 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][NH:15][CH:16]([CH3:18])[CH3:17])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[Cl:19][CH:20]([Cl:24])[C:21](Cl)=[O:22]>C1(C)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][N:15]([CH:16]([CH3:18])[CH3:17])[C:21](=[O:22])[CH:20]([Cl:24])[Cl:19])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 14798Sodium HydroxideHCID 1263584HCID 1263584, compound

Product 1

HCID 54004955HCID 54004955, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a sulfuration-flask, there is added while stirring 20 ml of 20% aqueous sodium hydroxide to 22,3 g of N-(3,4-dimethoxyphenylethyl)-N-isopropyl amine. The reaction mixture is then cooled in CO2 alcohol-cooling-bath to a temperature of -10° to -15°, to which is then added dropwise, while stirring a solution of 14.7 g of dichloroacetylchloride in 10 ml toluene. After everything has been added, the cooling-bath is removed and the reaction mixture is stirred for another 2 hours until it reaches room-temperature. It is then poured into an ice/water mixture and the organic material is extracted with toluene. The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate and concentrated in an rotatory evaporator. The title product is thus obtained as viscous oil in a yield of 28.4 g.

Workup

  1. additionIn a sulfuration-flask, there is added
  2. additionto which is then added dropwise
  3. additionAfter everything has been added
  4. customthe cooling-bath is removed
  5. additionIt is then poured into an ice/water mixture
  6. extractionthe organic material is extracted with toluene
  7. washThe toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in an rotatory evaporator

Sources & evidence

ORD record
ord-a8cc4c7f4c3b4caf90c7ac2b33cedc9d
Source dataset
uspto-grants-1990_01
Patent number
US04897109

Reaction notes

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