Citraconic Anhydrides → HCID 67073065, compound

HRID 1939406Notes

Reaction equation

HRID 1939406 reaction equation
[C:1]1([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.[C:11]1(=[O:18])[O:17][C:15](=[O:16])[CH:14]=[C:12]1[CH3:13]>CC(C)=O>[C:1]1([CH2:9][NH:10][C:15](=[O:16])/[CH:14]=[C:12](/[CH3:13])\[C:11]([OH:18])=[O:17])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:15](=[O:16])/[CH:14]=[C:12](/[CH3:13])\[C:11]([OH:17])=[O:18])[CH:2]=1

Participants

4

Reactant 2

HCID 12012Citraconic AnhydridesHCID 151331,3-Benzenedimethanamine

Product 1

HCID 67073065HCID 67073065, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A 2.5-liter glass resin kettle was charged with 136.2 g (1.0 mole) of m-xylylenediamine and 2000 ml of reagent acetone and flushed with nitrogen. The kettle was fitted with a dropping funnel, reflux condenser, mechanical stirrer and thermocouple. The addition funnel was charged with 246 g (2.2 moles) of citraconic anhydride which was slowly added over a 21/2-hour period, with stirring and refluxing the acetone. The reaction mixture was allowed to cool to room temperature with stirring. Suction filtering and acetone wash of the solid product (air-drying) gives a 246 g of a tan powder, melting at 148°-150° C. The structure was confirmed by NMR analysis.

Workup

  1. customflushed with nitrogen
  2. customThe kettle was fitted with a dropping funnel
  3. temperaturereflux condenser, mechanical stirrer
  4. additionwas slowly added over a 21/2-hour period
  5. stirringwith stirring
  6. filtrationSuction filtering
  7. washacetone wash of the solid product (air-drying)

Sources & evidence

ORD record
ord-eedc21b82c4d43de9650f62e09072066
Source dataset
uspto-grants-1997_12
Patent number
US05696188

Reaction notes

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