Methyl cyanoacetate → HCID 54383277, compound

HRID 1030767Notes

Reaction equation

HRID 1030767 reaction equation
[C:1]1([CH2:7][N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])#[N:25]>N1CCCCC1.CO>[C:18]1([CH2:17][N:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:9]2[CH:10]=[CH:11][C:12]([CH:13]=[C:26]([C:24]#[N:25])[C:27]([O:29][CH3:30])=[O:28])=[CH:15][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 7747Methyl cyanoacetateHCID 150959344-(Dibenzylamino)benzaldehyde

Product 1

HCID 54383277HCID 54383277, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(bis(phenylmethyl)amino]benzaldehyde (60.2 g, 0.20 mol), methyl cyanoacetate (21.8 g, 0.22 mol), methanol (300 mL), and piperidine (10 drops) is heated at reflux for 1.5 hours. After cooling, the yellow product is collected by filtration, washed with methanol, and dried in air. The yellow colorant, methyl 3-[4-[bis(phenylmethyl)amino]phenyl]-2-cyano-propenoate, is obtained in a yield of 53.5 g (70.0% of theory).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureAfter cooling
  4. filtrationthe yellow product is collected by filtration
  5. washwashed with methanol
  6. customdried in air

Sources & evidence

ORD record
ord-8dfbaf8ea5ab4eb7988ae65a6d7d812d
Source dataset
uspto-grants-1992_04
Patent number
US05106942

Reaction notes

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