Diethyl Ether → Penconazole

HRID 637516Notes

Reaction equation

HRID 637516 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:16][CH2:17][CH3:18])[CH2:10][NH:11][NH:12][C:13](=O)C.C(OCC)C.[OH-].[Na+].[Cl-].[CH3:27][N:28](C)C=NC=[N+](C)C>C(O)C.Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:16][CH2:17][CH3:18])[CH2:10][N:11]1[CH:27]=[N:28][CH:13]=[N:12]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 11008255Gold's ReagentHCID 20257012HCID 20257012, compound

Product 1

HCID 91693PenconazoleYield 86.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Conditions

Temperature
170 °C

Procedure

5.1 g (0.017 mol) of 1-[2-(2,4-dichlorophenyl)pentyl]-2acetylhydrazine in 10 ml of ethanol and 10 ml of concentrated hydrochloric acid are stirred at 50° C. overnight. The reaction mixture is then distributed between diethyl ether and 2 N sodium hydroxide solution; and the residue after concentration by evaporation is refluxed in 50 ml of absolute ethanol with 5.75 g (0.035 mol) of [3-(dimethylamino)-2-aza-prop-2-en-1-ylidene]-dimethylammonium chloride for 3.5 hours. The reaction solution is then concentrated by evaporation; 50 ml of formamide are added, and the mixture is heated at 170° C. for 1.5 hours. The reaction mixture, to which water has been added, is extracted with diethyl ether, and the residue obtained after concentration by evaporation is chromatographed to yield 4.2 g (84% of theory) of 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole.

Workup

  1. concentrationand the residue after concentration
  2. customby evaporation
  3. concentrationThe reaction solution is then concentrated by evaporation
  4. addition50 ml of formamide are added
  5. additionThe reaction mixture, to which water has been added
  6. extractionis extracted with diethyl ether
  7. customthe residue obtained
  8. concentrationafter concentration
  9. customby evaporation
  10. customis chromatographed

Sources & evidence

ORD record
ord-dd1c2a732b684b0f9df747792417a6ca
Source dataset
uspto-grants-1985_12
Patent number
US04556717

Reaction notes

Loading…