tert-Butyl acrylate → HCID 66678459, compound

HRID 2404316Notes

Reaction equation

HRID 2404316 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])[CH3:2].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[CH:14]=[CH2:15]>>[C:8]([C:7]1[CH:6]=[C:5]([CH:12]=[CH:11][CH:10]=1)[CH2:4][N:3]([CH2:1][CH3:2])[CH2:15][CH2:14][C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])#[N:9]

Participants

3

Reactant 2

HCID 15458tert-Butyl acrylateHCID 457596Benzonitrile, 3-((ethylamino)methyl)-

Product 1

HCID 66678459HCID 66678459, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 3-[(ethylamino)methyl]benzonitrile (5 g, 31 mmol) and tert-butyl acrylate (4.6 mL, 31 mmol) was heated neat at 80° C. for 12 hours. The crude mixture was purified by flash chromatography (silica, pet ether/EtOAc) to afford the title compound as colorless oil. 1H NMR (DMSO-d6, 400 MHz) δ 7.69 (m, 2H), 7.62 (d, J=7.8 Hz, 1H), 7.50 (m, 1H), 3.56 (s, 2H), 2.64 (t, 2H), 2.40 (m, 2H), 2.32 (t, 2H), 1.39 (s, 9H), 0.93 (t, 3H).

Workup

  1. customThe crude mixture was purified by flash chromatography (silica, pet ether/EtOAc)

Sources & evidence

ORD record
ord-bea8c71affb848c49c609aa9002f9f05
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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