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

HRID 574039

Reaction equation

HRID 574039 reaction equation
Cl.[C:2](=[NH:7])([O:4][CH2:5][CH3:6])[CH3:3].C(N(CC)CC)C.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:5]([O:4][C:2](=[N:7][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:3])[CH3:6]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 13028604Ethyl (1E)-N-benzoylethanimidateYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

First, 15.5 g of ethyl acetimidate hydrochloride, 150 mL of toluene, and 31.9 g of triethylamine (Et3N) were put into a 500-mL three-neck flask and stirred at room temperature for 10 minutes. With a 50-mL dropping funnel, a mixed solution of 17.7 g of benzoyl chloride and 30 mL of toluene were added dropwise to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, the reaction mixture was suction-filtered, and the solid was washed with toluene. The obtained filtrate was concentrated to give N-(1-ethoxyethylidene)benzamide (a red oily substance, 82% yield). A scheme of the synthesis of Step 1 is shown in the following (e-1).

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. filtrationthe reaction mixture was suction-filtered
  3. washthe solid was washed with toluene
  4. concentrationThe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-054ed1d128f9471588b200aa35f57463
Source dataset
uspto-grants-2015_05
Patent number
US09034486B2

Linked notes

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