Toluene → HCID 71073554, compound

HRID 1479130Notes

Reaction equation

HRID 1479130 reaction equation
Cl.[C:2](=[NH:12])([O:9]CC)[C:3]1[CH:8]=[CH:7]C=CC=1.C(N(CC)CC)C.[C:20](Cl)(=[O:24])[CH2:21]CC.[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:20]([O:24][C:26]1([CH:31]=[CH:30][CH:29]=[CH:28][CH2:27]1)[CH:32]=[N:12][C:2](=[O:9])[CH2:3][CH2:8][CH3:7])[CH3:21]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 71073554HCID 71073554, 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 this mixture was stirred at room temperature for 10 minutes. After a predetermined time elapsed, with a 50-mL dropping funnel, a mixed solution of 5.8 g of butyryl chloride and 30 mL of toluene was added dropwise to this mixture, and the mixture was stirred at room temperature for 24 hours. After the stirring, this mixture was suction-filtered, and the obtained filtrate was concentrated to give N-(1-ethoxybenzylidene)butyramide (a yellow oily substance, 100% yield). The synthesis scheme of Step 1 is shown in (A-1) below.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. filtrationAfter the stirring, this mixture was suction-filtered
  3. concentrationthe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-dbcb8d7599e441a9b92121a8b86c13f1
Source dataset
uspto-grants-2016_08
Patent number
US09406894B2

Reaction notes

Loading…