Toluene → HCID 86674301, compound

HRID 1479132Notes

Reaction equation

HRID 1479132 reaction equation
Cl.[C:2](=[NH:12])([O:9]CC)[C:3]1C=CC=CC=1.C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21].[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:20]([O:22][C:24]1([CH:29]=[CH:28][CH:27]=[CH:26][CH2:25]1)[CH:30]=[N:12][C:2](=[O:9])[CH3:3])[CH3:21]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 86674301HCID 86674301, compoundYield 100%

Procedure

First, 10 g of ethyl benzimidate hydrochloride, 150 mL of toluene, and 11 g of triethylamine (Et3N) were put into a 500-mL three-neck flask and the mixture was stirred at room temperature for 10 minutes. After a predetermined time elapsed, with a 50-mL dropping funnel, a mixed solution of 3.8 g of acetyl chloride and 30 mL of toluene was added dropwise to this mixture, and the mixture was stirred at room temperature for 24 hours. The obtained mixture was suction-filtered, and the obtained filtrate was concentrated to give N-(1-ethoxybenzylidene)acetamide (a yellow oily substance, 100% yield). The synthesis scheme of Step 1 is shown in (B-1) below.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. filtrationThe obtained mixture was suction-filtered
  3. concentrationthe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-0c9ec3af26aa4044b5c539a2cfc3b1ec
Source dataset
uspto-grants-2016_08
Patent number
US09406894B2

Reaction notes

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