Octyl cyanoacetate → HCID 86678045, compound

HRID 1852324Notes

Reaction equation

HRID 1852324 reaction equation
N(C=CC=O)C1C=CC=CC=1.NC1C=CC=CC=1.[C:19]([CH2:21][C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:23])#[N:20].[C:33]([N:36]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)/[CH:37]=[CH:38]/[CH:39]=C(\C#N)/C(OCCCC)=O)(=[O:35])[CH3:34]>C(OC(=O)C)(=O)C>[C:33]([N:36]([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)/[CH:37]=[CH:38]/[CH:39]=[C:21](\[C:19]#[N:20])/[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:23])(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 4384482Octyl cyanoacetateHCID 86678046HCID 86678046, compoundHCID 86678047HCID 86678047, compound

Product 1

HCID 86678045HCID 86678045, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

3-Anilinoacrolein-aniline (27.7 g, 0.125 mol) and n-octyl cyanoacetate (26.3 ml, 0.125 mol) are heated in 70 ml of acetic anhydride at 115° C. for 2 hours while bubbling with nitrogen. After cooling, 80 ml of methanol are added and precipitation is allowed to take place. The solid obtained is filtered off and rinsed with methanol. Drying is carried out. 36.4 g of a yellow powder (yield: 79%) of butyl (2E,4E)-5-[acetyl(phenyl)amino]-2-cyanopenta-2,4-dienoate are recovered, which powder is used as is in the following stage.

Workup

  1. customwhile bubbling with nitrogen
  2. temperatureAfter cooling
  3. addition80 ml of methanol are added
  4. customprecipitation
  5. customThe solid obtained
  6. filtrationis filtered off
  7. washrinsed with methanol
  8. customDrying

Sources & evidence

ORD record
ord-37844cefff924f919cc756a4081d5af5
Source dataset
uspto-grants-2015_02
Patent number
US08961941B2

Reaction notes

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