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 1013708Notes

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 Found m/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-0aa114255ee4494dba159188fba1e3db
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981891B2

Reaction notes

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