N-Cyanoacetylethylcarbamate → (E,E)-[2-Cyano-5-(3,4-dihydroxyphenyl)-penta-2,4-dienoyl]carbamic acid ethyl ester

HRID 1818043

Reaction equation

HRID 1818043 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:5]=[CH:6][CH:7]=O.[C:13]([CH2:15][C:16]([NH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:17])#[N:14]>>[CH2:22]([O:21][C:19](=[O:20])[NH:18][C:16](=[O:17])/[C:15](/[C:13]#[N:14])=[CH:7]/[CH:6]=[CH:5]/[C:4]1[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([OH:1])[CH:3]=1)[CH3:23]

Participants

3

Reactant 2

HCID 23112N-CyanoacetylethylcarbamateHCID 4430343-(3,4-Dihydroxy-phenyl)-2-propenal

Product 1

HCID 11460833(E,E)-[2-Cyano-5-(3,4-dihydroxyphenyl)-penta-2,4-dienoyl]carbamic acid ethyl ester

Procedure

The compound was prepared as described in Example 3 by adding 3,4-dihydroxycinnamaldehyde (32 mg, 0.2 mmol) to N-cyanoacetylurethane (32 mg, 0.2 mmol). After refluxing for 1 h and recrystallization from ethanol-water an orange solid was obtained (54 mg, 90%). The product gave the following analytical data:

Workup

  1. customThe compound was prepared
  2. temperatureAfter refluxing for 1 h
  3. customrecrystallization from ethanol-water an orange solid
  4. customwas obtained (54 mg, 90%)
  5. customThe product gave the following analytical data

Sources & evidence

ORD record
ord-d291ff31e2a94a55bc38202343890f7c
Source dataset
uspto-grants-2009_10
Patent number
US07598419B2

Linked notes

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