Triethylamine → HCID 86657768, compound

HRID 2381266Notes

Reaction equation

HRID 2381266 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10][CH2:11][C:12](=O)[CH3:13].C(N(CC)CC)C.Cl.[CH3:23][O:24][NH2:25]>CO.O>[CH3:23][O:24][N:25]=[C:12]([CH2:11][CH2:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=1[Cl:9])[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 58231449HCID 58231449, compound

Product 1

HCID 86657768HCID 86657768, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-(2,4,6-trichloro-phenyl)-butan-2-one (0.9 g, 3.57 mmol) in methanol (5 ml), was added triethylamine (0.73 ml, 5.3 mmol) and O-methyl-hydroxylamine hydrochloride (0.447 g, 5.3 mmol). The reaction mixture was heated at a temperature of 60° C. for 3 hours. When the TLC confirmed the completion of the reaction, the reaction mass was allowed to attain ambient temperature. After the reaction mixture was diluted with water and methanol was evaporated off, the aqueous layer was extracted with ethyl acetate (3×30 ml). The combined ethyl acetate layers were washed with water followed by brine solution and dried over sodium sulfate before complete evaporation of the solvents to give 4-(2,4,6-trichloro-phenyl)-butan-2-one O-methyl-oxime (0.980 g) crude, which was taken up for reduction without any further purification.

Workup

  1. customthe completion of the reaction
  2. customto attain ambient temperature
  3. customwas evaporated off
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×30 ml)
  5. washThe combined ethyl acetate layers were washed with water
  6. dry with materialdried over sodium sulfate before complete evaporation of the solvents

Sources & evidence

ORD record
ord-70565df18f0b4928a0513370a993db41
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

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