Water → HCID 19756490, compound

HRID 1587765Notes

Reaction equation

HRID 1587765 reaction equation
[Br:1]Br.[OH-].[Na+].[C:5]([C:7]([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1)([CH2:14][CH:15]=[CH2:16])[CH2:8][N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)#[N:6].O>O1CCOCC1>[C:5]([C:7]([C:17]1[CH:18]=[CH:19][C:20]([C:23]#[C:24][Br:1])=[CH:21][CH:22]=1)([CH2:14][CH:15]=[CH2:16])[CH2:8][N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 19756488α-(4-Ethynylphenyl)-α-2-propen-1-yl-1H-1,2,4-triazole-1-propanenitrile

Product 1

HCID 19756490HCID 19756490, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.8 g of bromine are added, at 0°, to 5 ml of 10% NaOH while stirring vigorously. After the solution has become colourless a solution of 1 g 2-cyano-2-(4-ethinylphenyl)-1-(1H-1,2,4-triazol-1-yl)-4-pentene in 3 ml of dioxane are added dropwise, at 0°, within a few minutes. The reaction mixture is then stirred for 3 hours at room temperature, poured into 100 ml of water, extracted with diethylether, the ether extract washed with water (3 times), dried and the ether evaporated. The residue is heated for 3 hours at high vacuum and a temperature of 50°-60° C. The thus obtained title compound has a Rf value of 0.75, employing CH2Cl2 /CH3OH 9:1 as eluant (Compound 4).

Workup

  1. additionare added dropwise, at 0°, within a few minutes
  2. stirringThe reaction mixture is then stirred for 3 hours at room temperature
  3. extractionextracted with diethylether
  4. extractionthe ether extract
  5. washwashed with water (3 times)
  6. customdried
  7. customthe ether evaporated
  8. temperatureThe residue is heated for 3 hours at high vacuum
  9. customa temperature of 50°-60° C

Sources & evidence

ORD record
ord-3b4e291d37a8428cad2af9dfb752bfcf
Source dataset
uspto-grants-1993_06
Patent number
US05219876

Reaction notes

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