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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 503583
Notes
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Reaction equation

HRID 503583 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 663013,5-Dimethoxyaniline

Product 1

HCID 673176235-(((3,5-Dimethoxyphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

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

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

Sources & evidence

ORD record
ord-720c9190697c4f8eaa80a72ee47b3c43
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07776857B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes