Dichloroacetyl chloride → HCID 19826626, compound

HRID 1086138Notes

Reaction equation

HRID 1086138 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]([NH:15][CH3:16])[C:13]#[N:14]>C1(C)C=CC=CC=1.O.[OH-].[Na+]>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]([N:15]([CH3:16])[C:3](=[O:4])[CH:2]([Cl:6])[Cl:1])[C:13]#[N:14]

Participants

6

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 43114997HCID 43114997, compound

Product 1

HCID 19826626HCID 19826626, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 14.7 g of dichloroacetylchloride in 10 ml of toluene are added dropwise, while stirring at a temperature of -10° to 15° C. to another solution of 20.6 g of N-(3,4-dimethoxy-α-cyanobenzyl-N-methylamine (prepared according to J. Prakt. Chem. 285 (1961) p. 258) in 80 ml of toluene and 20 ml of water, in which was dissolved 4 g of solid NaOH. A solid reaction product precipitates, which is filtered and washed with water until the aqueous filtrate is neutral. The solid acid amide is dried under vacuum to yield 27.7 g of raw product melting at 102°. After treating it with charcoal and recrystallisation from ethanol one obtains 125 g of crystalline title product, melting at 111°-112°.

Workup

  1. customA solid reaction product
  2. customprecipitates
  3. filtrationwhich is filtered
  4. washwashed with water until the aqueous filtrate
  5. dry with materialThe solid acid amide is dried under vacuum
  6. customto yield 27.7 g of raw product melting at 102°
  7. additionAfter treating it
  8. customwith charcoal and recrystallisation from ethanol one

Sources & evidence

ORD record
ord-63f4d1421ac64ee4b8b552c0ff304df8
Source dataset
uspto-grants-1991_07
Patent number
US05028256

Reaction notes

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