Toluene → N,N-bis[3-(2-ethoxycarbonylethyl)phenyl]-3,4-xylidine

HRID 1451663Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1.I[C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=1)[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:24](=[O:27])([O-])[O-:25].[K+].[K+].CCCCC[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[C:43]1(C)C=CC=C[CH:44]=1>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:19]([O:18][C:16]([CH2:15][CH2:14][C:13]1[CH:12]=[C:11]([N:1]([C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([CH2:36][CH2:35][C:24]([O:25][CH2:43][CH3:44])=[O:27])[CH:42]=2)[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=2)[CH:23]=[CH:22][CH:21]=1)=[O:17])[CH3:20]

Participants

Conditions

Temperature: 230 °C

Procedure

Into a 100-ml flask were introduced 0.6 g of 3,4-xylidine, 3.4 g of ethyl 3-iododihydrocinnamate, 1.9 g of potassium carbonate, 0.5 g of copper sulfate pentahydrate, and 5 ml of n-tridecane. The reactants were reacted with heating at 230° C. for 10 hours under an atmosphere of nitrogen. After the reaction, the reaction mixture was cooled to room temperature and then dissolved into 50 ml of toluene. Insolubles were filtered off, and the filtrate was purified by silica gel column chromatography using toluene. As a result, 2.0 g of N,N-bis[3-(2-ethoxycarbonylethyl)phenyl]-3,4-xylidine was obtained as an oily substance. An IR spectrum of this compound is shown in FIG. 2.

Workup

customThe reactants were reacted
customAfter the reaction
temperaturethe reaction mixture was cooled to room temperature
filtrationInsolubles were filtered off
customthe filtrate was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-09bbcd5c59554638846360d41fa1a3d5
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05604064

Reaction notes

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