Benzoyl chloride → Ethyl (1E)-N-benzoylethanimidate

HRID 720703Notes

Reaction equation

HRID 720703 reaction equation
Cl.C([CH2:4][C:5]([NH2:7])=[O:6])C.[CH2:8](N(CC)CC)[CH3:9].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[CH2:8]([O:6][C:5](=[N:7][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:4])[CH3:9]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22560754Butanamide--hydrogen chloride (1/1)

Product 1

HCID 13028604Ethyl (1E)-N-benzoylethanimidateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethylacetamidate hydrochloride 1.0 g (8.09 mmol) was dissolved in dichloromethane 40 ml at room temperature, added dropwise triethylamine 1.08 ml (16.99 mmol) and stirred for 30 minutes at room temperature. Then, the reacting solution was cooled to 0° C., benzoylchloride 1.03 g (7.35 mmol) was slowly added dropwise in the reacting solution for 10 minutes and stirred for 4 hours at room temperature. After completing the reaction, the reacting solution was washed with water and saturated brine, and then dried with anhydrous magnesium sulfate. Then, the resulting product was filtered under reduced pressure and purified through a flash column chromatography (ethyl acetate:normal hexane=2:8). As a result, N-(1-ethoxy-ethylidene)-benzamide (1.20 g, yield: 86%) was obtained as a liquid phase.

Workup

  1. temperatureThen, the reacting solution was cooled to 0° C.
  2. stirringstirred for 4 hours at room temperature
  3. customthe reaction
  4. washthe reacting solution was washed with water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationThen, the resulting product was filtered under reduced pressure
  7. custompurified through a flash column chromatography (ethyl acetate:normal hexane=2:8)

Sources & evidence

ORD record
ord-fab31886fef84f30984d68921003bee9
Source dataset
uspto-grants-2006_11
Patent number
US07135572B2

Reaction notes

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