Acetic Acid → 2-[4-(Trimethylsilanylmethoxy)benzylidene]malonamide

HRID 899021Notes

Reaction equation

HRID 899021 reaction equation
[CH3:1][Si:2]([CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)([CH3:4])[CH3:3].[C:15]([NH2:21])(=[O:20])[CH2:16][C:17]([NH2:19])=[O:18].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:1][Si:2]([CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[C:16]([C:15]([NH2:21])=[O:20])[C:17]([NH2:19])=[O:18])=[CH:9][CH:8]=1)([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7911MalonamideHCID 8082PiperidineHCID 565289644-Trimethylsilanylmethoxybenzaldehyde

Product 1

HCID 101083992-[4-(Trimethylsilanylmethoxy)benzylidene]malonamideYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-(Trimethylsilanylmethoxy)benzaldehyde (obtained in step 1 of Example 1) (10.4 g, 0.005 mol) and malonamide (5.5 g, 0.055 mol) in 20 ml of dry toluene in the presence of 0.5 ml of piperidine and 0.3 g of acetic acid are refluxed for 3 hours in a reactor equipped with Dean-Stark apparatus. The water formed is removed azeotropically. The mixture is cooled and the organic phase is washed twice with water. The organic phase is dried over sodium sulfate and filtered, and the solvent is evaporated off under vacuum. After recrystallization from ethanol, 7.2 g (yield: 49%) of the derivative of Example 10 are obtained in the form of an off-white powder:

Workup

  1. customequipped with Dean-Stark apparatus
  2. customis removed azeotropically
  3. temperatureThe mixture is cooled
  4. washthe organic phase is washed twice with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated off under vacuum
  8. customAfter recrystallization from ethanol, 7.2 g (yield: 49%) of the derivative of Example 10
  9. customare obtained in the form of an off-white powder

Sources & evidence

ORD record
ord-cc4c636fed4448b8bbc95fc511865ee1
Source dataset
uspto-grants-2008_04
Patent number
US07354571B2

Reaction notes

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