Acetic Acid → HCID 86678050, compound

HRID 1852327Notes

Reaction equation

[C:1](O)(=O)C.[CH2:5]([NH2:13])CCCCCCC.[C:14]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:18])#[N:15].[C:28]1([CH3:34])C=CC=C[CH:29]=1>>[C:14](/[C:16](=[CH:34]\[CH:28]=[CH:29]\[N:13]([CH3:5])[CH3:1])/[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:18])#[N:15]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 1140Toluene

HCID 8143Octylamine

HCID 4384482Octyl cyanoacetate

Product 1

HCID 86678050HCID 86678050, compoundYield 85%

Procedure

N,N-Dimethylacrolein (37.4 ml, 0.374 mol) is dissolved in 500 ml of toluene while bubbling with nitrogen and the catalyst, a mixture of acetic acid (4.1 ml, 0.2 equiv.) and of n-octylamine (1.8 ml, 0.03 equiv.), is added. The mixture is heated to reflux and n-octyl cyanoacetate (76 ml, 0.359 mol) is added dropwise over 25 minutes. The water is removed by azeotropic distillation. The reaction is halted after 2 hours. The solvent is evaporated under vacuum. 123 g of an orangey brown solid are obtained, which solid is recrystallized from isopropanol to give 118.5 g (yield: 85%) of the derivative of Example 7 in the form of pale yellow needles:

Workup

customwhile bubbling with nitrogen
temperatureThe mixture is heated
temperatureto reflux
customThe water is removed by azeotropic distillation
customThe solvent is evaporated under vacuum

Sources & evidence

ORD record: ord-bfc484c753de4d58a1ed1330e93d33d7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08961941B2

Reaction notes

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