2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(((3,5-Dimethoxyphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 503593Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[CH:11](OCC)(OCC)OCC.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH2:31])[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1>CCCCCC>[CH3:30][O:29][C:27]1[CH:26]=[C:25]([NH:31][CH:11]=[C:5]2[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:9])[CH:24]=[C:23]([O:22][CH3:21])[CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a dried 2-necked round bottom flask equipped with reflux condenser and inert atmosphere, 2,2-dimethyl-1,3-dioxane-4,6-dione (5.3 g, 37 mmol) was dissolved in triethyl orthoformate (37 ml, 221 mmol) and the mixture was stirred at 100° C. under nitrogen for 1.5 h. 3,5-dimethoxybenzenamine (5.6 g, 37 mmol) was added and heating continued for 4.5 h. The reaction mixture was cooled down to RT and poured into hexane (50 mL). The solid was filtered off and washed with hexane to afford 5-((3,5-dimethoxyphenylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione as a light yellow solid. MS: W/z=[M+H]+. 308.1 Calc'd for C15H17NO6: 307.3.

Workup

customIn a dried 2-necked round bottom flask equipped
temperaturewith reflux condenser
temperatureheating
waitcontinued for 4.5 h
temperatureThe reaction mixture was cooled down to RT
filtrationThe solid was filtered off
washwashed with hexane

Sources & evidence

ORD record: ord-ea56e81fd44e45c4a9fdeee7707ceb13
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776857B2

Reaction notes

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