Diethyl Ether → HCID 19090134, compound

HRID 1084911Notes

Reaction equation

HRID 1084911 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.[Mg].[CH3:11][N:12]([CH3:21])[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#N.CC[O:24]CC>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([N:12]([CH3:21])[CH3:11])[CH:14]=2)=[O:24])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether3×HCID 12103m,alpha-DichlorotolueneHCID 34538793-(dimethylamino)benzonitrileHCID 5462224Magnesium

Product 1

HCID 19090134HCID 19090134, compound

Procedure

A solution of 10.0 g of 3-chlorobenzyl chloride in 100 ml of dry ether was added slowly to 2.26 g of magnesium in 75 ml of dry ether under nitrogen. The Grignard reagent was stirred at ambient temperature for one hour and then added to a solution of 4.5 g of 3-dimethylaminobenzonitrile in 150 ml of dry ether. After the addition a catalytic amount of CuBr was added and the solution stirred overnight. The reaction was quenched with 200 ml of ammonium chloride solution and diluted with water. The layers were separated and the aqueous phase extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel: 8:1 hexane-ethyl acetate) and then treated with ethereal HCl until acidic to wet litmus paper. The precipitate was collected and recrystallized from ethanol-ether to give 3.8 g of 2-(3-chlorophenyl)1-[3-(dimethylamino)phenyl]ethanone hydrochloride, m.p. 92°-94° C.

Workup

  1. additionwas added
  2. customThe reaction was quenched with 200 ml of ammonium chloride solution
  3. additiondiluted with water
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (silica gel: 8:1 hexane-ethyl acetate)
  10. additiontreated with ethereal HCl until acidic to wet litmus paper
  11. customThe precipitate was collected
  12. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-b8279d5ee51d493d81dc7a1f8a892707
Source dataset
uspto-grants-1991_04
Patent number
US05006563

Reaction notes

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