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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 1013708
Notes
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Reaction equation

HRID 1013708 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-0aa114255ee4494dba159188fba1e3db
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981891B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes