Toluene → HCID 71073579, compound

HRID 1479136Notes

Reaction equation

HRID 1479136 reaction equation
Cl.C1C2C(=CC=CC=2)[CH:5]=[CH:4][C:3]=1[C:12](=[NH:16])[O:13]CC.[CH2:17](N(CC)CC)[CH3:18].[C:24](Cl)(=[O:28])[CH2:25][CH2:26][CH3:27].[C:30]1(C)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:17]([O:28][CH:24]1[C:31]2[C:30](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:26][C:25]1=[N:16][C:12](=[O:13])[CH2:3][CH2:4][CH3:5])[CH3:18]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 866743024278-14-2

Product 1

HCID 71073579HCID 71073579, compoundYield 100%

Procedure

First, 5 g of ethyl 2-naphthalenecarboximidate hydrochloride, 50 mL of toluene, and 4.3 g of triethylamine (Et3N) were put into a 300-mL three-neck flask and the mixture was stirred at room temperature for 10 minutes. With a 50-mL dropping funnel, a mixed solution of 2.3 g of butyryl chloride and 30 mL of toluene was added dropwise to this mixture, and the mixture was stirred at room temperature for 41.5 hours. After a predetermined time elapsed, the reaction mixture was suction-filtered, and the filtrate was concentrated to give N-(1-ethoxy-2-naphthylidene)butyramide (a yellow oily substance, 100% yield). The synthesis scheme of Step 1 is shown in (F-1) below.

Workup

  1. stirringthe mixture was stirred at room temperature for 41.5 hours
  2. filtrationthe reaction mixture was suction-filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9acde506d1f4435390956d581d1a9b64
Source dataset
uspto-grants-2016_08
Patent number
US09406894B2

Reaction notes

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