Ammonia → 5-amino-3-ethyl-1-(2-octyl)-1H-pyrazole-4-carboxamide

HRID 566325

Reaction equation

HRID 566325 reaction equation
C(O[C:4](=[C:7]([C:10]#[N:11])[C:8]#[N:9])[CH2:5][CH3:6])C.[CH3:12][CH:13]([NH:20][NH2:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].N.[OH:23]O>CO.C(O)C>[NH2:9][C:8]1[N:20]([CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:12])[N:21]=[C:4]([CH2:5][CH3:6])[C:7]=1[C:10]([NH2:11])=[O:23]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 20811OctamoxinHCID 2314702-(1-Ethoxypropylidene)malononitrile

Product 1

HCID 599323425-amino-3-ethyl-1-(2-octyl)-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

5.21 g (34.66 mmol) of 2-(1-ethoxy-propylidene)-malononitrile and 5.00 g (34.66 mmol) of (1-methyl-heptyl)-hydrazine are refluxed for 4 hours in 40 ml of methanol. After the solvent has been removed in vacuo, 8.60 g of a red oil are obtained. The latter is dissolved in 250 ml of ethanol and, after 300 ml of concentrated NH3 solution (25% strength) and 70 ml of hydrogen peroxide solution (30%) have been added, the mixture is stirred for 48 hours at room temperature. After the non-aqueous solvents have been removed, the mixture is extracted three times with dichloromethane, and the organic phase is dried over sodium sulphate and evaporated on a rotary evaporator. This gives 7.45 g (71%) of a red solid.

Workup

  1. customAfter the solvent has been removed in vacuo, 8.60 g of a red oil
  2. customare obtained
  3. customAfter the non-aqueous solvents have been removed
  4. extractionthe mixture is extracted three times with dichloromethane
  5. dry with materialthe organic phase is dried over sodium sulphate
  6. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-b26457991c0a435db9c81e60e77aa380
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Linked notes

Loading…