Hydrazinecarboxylic acid, ethyl ester → N'-(2-Cyclopropylethylidene)hydrazinecarboxylic acid ethyl ester

HRID 30981

Reaction equation

HRID 30981 reaction equation
[CH:1]1([CH2:4][CH:5]=O)[CH2:3][CH2:2]1.[C:7]([O:11][CH2:12][CH3:13])(=[O:10])[NH:8][NH2:9]>CCO>[CH2:12]([O:11][C:7]([NH:8][N:9]=[CH:5][CH2:4][CH:1]1[CH2:2][CH2:3]1)=[O:10])[CH3:13]

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 103078492-Cyclopropylacetaldehyde

Product 1

HCID 69310105N'-(2-Cyclopropylethylidene)hydrazinecarboxylic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The solution of 2-cyclopropylethanal was diluted with 50 mL EtOH. Ethyl carbazate (5.14 g, 49.3 mmol) was added and the solution stirred at room temperature for 12 h, upon which it was concentrated in vacuo and the crude material was purified by flash column chromatography (0-5% MeOH in CH2Cl2) to give 7.1 g (85%) of the hydrazone (4a) as a colorless crystalline solid. 1H-NMR (400 MHz, CDCl3): 8.21 (br s, 1H); 7.21 (s, 1H); 4.23 (m, 2H); 2.17 (t, 3H, J=5.9 Hz) 1.06 (m, 2H); 0.80 (m, 1H); 0.1 (d, 2H); 0.48 (m, 2H); 0.13 (m, 2H) ppm.

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe crude material was purified by flash column chromatography (0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4b3a774da7f34e66bb4f679f126c9102
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Linked notes

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