Dichloroacetyl chloride → HCID 19826618, compound

HRID 330458Notes

Reaction equation

HRID 330458 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH2:7][NH:8][CH:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=1.[Cl:16][CH:17]([Cl:21])[C:18](Cl)=[O:19]>>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:13]=[CH:12][C:6]([CH2:7][N:8]([CH:9]([CH3:11])[CH3:10])[C:18](=[O:19])[CH:17]([Cl:21])[Cl:16])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 19826566N-(1-Methylethyl)-4-(trifluoromethyl)benzenemethanamine

Product 1

HCID 19826618HCID 19826618, compoundYield 66.3%

Procedure

A solution of 21.7 g of N-(4-trifluoromethylbenzyl)-N-isopropyl-amine is added while stirring in a 4 neck-flask with 20 ml of 20% sodium-hydroxide solution. The reaction-mixture is then cooled while stirring in an alcohol/CO2 -bath to a temperature of from -10° to -5° whereupon 14.7 g of dichloroacetyl chloride is added slowly, dropwise thereto. After about 1/2 hour, when everything is added, the cooling-bath is removed and the reaction mixture is stirred for 2 hours until it reaches room temperature. It is then poured into ice/water and the organic material is extracted with toluene. The toluene-phases are collected washed first with diluted sodium hydroxide, then with diluted hydrochloric acid and eventually twice with water, dried over sodium sulfate and concentrated in a rotatory evaporator. A clear oil is thus obtained, which becomes solid after a while. The solid mass is then triturated with hexane and filtered to yield 21.7 g of crystalline N-(4-trifluoromethylbenzyl)-N-isopropyl-dichloroacetamide, melting at 92° to 93°.

Workup

  1. temperatureThe reaction-mixture is then cooled
  2. additionis added slowly
  3. additionwhen everything is added
  4. customthe cooling-bath is removed
  5. stirringthe reaction mixture is stirred for 2 hours until it
  6. customreaches room temperature
  7. additionIt is then poured into ice/water
  8. extractionthe organic material is extracted with toluene
  9. customThe toluene-phases are collected
  10. washwashed first with diluted sodium hydroxide
  11. dry with materialwith diluted hydrochloric acid and eventually twice with water, dried over sodium sulfate
  12. concentrationconcentrated in a rotatory evaporator
  13. customA clear oil is thus obtained
  14. customThe solid mass is then triturated with hexane
  15. filtrationfiltered

Sources & evidence

ORD record
ord-9bddf4b37e0144398f334a6f9fbb9b33
Source dataset
uspto-grants-1990_01
Patent number
US04897109

Reaction notes

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