Toluene → HCID 9886503, compound

HRID 263974Notes

Reaction equation

HRID 263974 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:3]=1[CH:4]=O.[C:12]([CH2:15][C:16](=[O:18])[CH3:17])(=O)[CH3:13].Cl.[CH3:20][NH2:21].[C:22]1([CH3:28])C=CC=C[CH:23]=1.CCO[C:32]([CH3:34])=[O:33]>N1C=CC=CC=1>[C:16]([C:15]1[CH:4]([C:3]2[CH:6]=[C:7]([Cl:11])[C:8]([Cl:10])=[CH:9][C:2]=2[Cl:1])[C:23]([C:32](=[O:33])[CH3:34])=[C:22]([CH3:28])[N:21]([CH3:20])[C:12]=1[CH3:13])(=[O:18])[CH3:17]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 31261AcetylacetoneHCID 6101942,4,5-TrichlorobenzaldehydeHCID 6364545Methylamine hydrochloride

Product 1

HCID 9886503HCID 9886503, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

5.0 g (23.9 mmol) of 2,4,5-trichlorobenzaldehyde, 4.8 g (47.8 mmol) of acetylacetone and 1.78 g (26.3 mmol) of methylamine hydrochloride are boiled under reflux for 5 h in 4 ml of pyridine. The pyridine is then stripped off and the residue is codistilled twice with toluene. It is taken up in AcOEt and the solution is extracted with 1N aqueous HCl. Drying and concentration of the aqueous phase yields a brown oil, which is purified by flash chromatography (petroleum ether/AcOEt=5:1). The product is finally recrystallized from ether. 4.2 g of the title compound (45% of theory) are obtained. MS:385 Rf =0.65 (petroleum ether: AcOEt:=1:1)

Workup

  1. extractionthe solution is extracted with 1N aqueous HCl
  2. customDrying
  3. customconcentration of the aqueous phase yields a brown oil, which
  4. customis purified by flash chromatography (petroleum ether/AcOEt=5:1)
  5. customThe product is finally recrystallized from ether

Sources & evidence

ORD record
ord-0cfd4616a44744afb99f2c2b5fb03d06
Source dataset
uspto-grants-1997_07
Patent number
US05646166

Reaction notes

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