ethyl N-ethoxycarbonyliminocarbamate → HCID 53698348, compound

HRID 1378919Notes

Reaction equation

HRID 1378919 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[CH:11]=[CH:12][CH:13]=[CH2:14])[CH3:2].[CH2:16]([O:18][C:19]([N:21]=[N:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:20])[CH3:17]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[CH:11]1[CH:12]=[CH:13][CH2:14][N:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]1[C:19]([O:18][CH2:16][CH3:17])=[O:20])[CH3:2]

Participants

4

Reactant 2

HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 54563406HCID 54563406, compound

Product 1

HCID 53698348HCID 53698348, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.8 g of 2-(1,3-butadienyl)nicotinic acid ethyl ester and 9.2 g of diethyl-azodicarboxylate are mixed with 30 ml of toluene and heated to 80° under nitrogen. After 1 hr a further 3 g of diethyl-azodicarboxlate are added and after 3 hrs a further 5 g. After a further 4 hrs the reaction mixture is allowed to cool to RT and stirred overnight. The solvent is removed by evaporation under vacuum and the resulting oil chromatographed on silica gel and eluted with ethylacetate/hexane to give the title compound as black oil.

Workup

  1. temperatureheated to 80° under nitrogen
  2. customThe solvent is removed by evaporation under vacuum
  3. customthe resulting oil chromatographed on silica gel
  4. washeluted with ethylacetate/hexane

Sources & evidence

ORD record
ord-432e67d450ec4b79a9776020438637d2
Source dataset
uspto-grants-1997_09
Patent number
US05670456

Reaction notes

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