Ethanolamine → HCID 54276884, compound

HRID 1387347Notes

Reaction equation

HRID 1387347 reaction equation
[CH2:1]([CH2:3]N)[OH:2].C1(C)C(C)=CC=CC=1.[Cl:13][C:14]1[CH:33]=[CH:32][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](=[N:29][O:30][CH3:31])[C:27]#[N:28])=[CH:16][CH:15]=1>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.O>[CH3:31][O:30][N:29]=[C:26]([C:27]1[O:2][CH2:1][CH2:3][N:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][CH2:18][C:17]1[CH:16]=[CH:15][C:14]([Cl:13])=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 7237O-XyleneHCID 865846762-(4-Chlorobenzyloxy)-alpha-methoxyiminophenylacetonitrile

Product 1

HCID 54276884HCID 54276884, compoundYield 9.8%

Reagents, catalysts & solvents 2

HCID 2724192Zinc acetate (USP)CatalystHCID 962WaterSolvent

Procedure

Zinc acetate dihydrate (400 mg, 1.8 mmol), ethanolamine (975 mg, 15.9 mmol) and xylene (8 ml) were added to 2-(4-chlorobenzyloxy)-α-methoxyiminophenylacetonitrile (4.00 g, 13.3 mmol), and the mixture was stirred under reflux for 63 hours. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give isomer A (1.31 g, 28.6%, as crystals) and isomer B (0.45 g, 9.8%, as crystals) of 2-(4-chlorobenzyloxy)phenyl 2-oxazolin-2-yl ketone O-methyloxime.

Workup

  1. temperatureunder reflux for 63 hours
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-8e4fcdd63bbd4351abbcdb801ed1f2c7
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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