Hexane → HCID 72828588, compound

HRID 709397Notes

Reaction equation

HRID 709397 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14]C>>[C:1]([O:5][C:6]([NH:7][N:8]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8058HexaneHCID 70091tert-Butyl carbazate

Product 1

HCID 72828588HCID 72828588, compoundYield 89%

Procedure

A solution of valeraldehydede (2.0 g; 23 mmoles) and t-butylcarbazate (3.1 g; 23 mmoles) in hexane (25 mL) is heated under reflux conditions for 30 minutes. At the end the solution is cooled at room temperature. The solvent is removed under vacuum and the obtained residue purified by chromatography on silica gel eluting with chloroform. 4.1 g of t-butyl-2-pentylidenhydrazinecarboxylate (white solid; yield 89%) are obtained. Rf=0.32 chloroform; 1H NMR (CDCl3) δ (ppm): 8.02 (s broad, 1H, NH), 7.19 (t, 1H, CH), 2.29 (m, 2H, CH2), 1.46 (m, 11H, CH2 and CH3), 1.36 (m, 2H, CH2), 0.91 (t, 3H, CH3); 13C NMR (CDCl3) δ (ppm): 147.6, 146.7, 80.8, 31.9, 28.8, 28.3, 22.3, 13.8.

Workup

  1. customThe solvent is removed under vacuum
  2. customthe obtained residue purified by chromatography on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-c1f9e9ec87a64f549bfc93aef470618c
Source dataset
uspto-grants-2015_11
Patent number
US09181196B2

Reaction notes

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