1H-1,2,4-Triazole → HCID 54087959, compound

HRID 225007Notes

Reaction equation

HRID 225007 reaction equation
[CH3:1][C:2]([CH3:14])([C:4](=[O:13])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:3].BrBr.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.[H-].[Na+]>C(Cl)(Cl)(Cl)Cl.CN(C)C=O.O>[CH3:3][C:2]([CH3:14])([C:4](=[O:13])[CH:5]=[C:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[CH3:1]

Participants

8

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24408BromineHCID 24758Sodium hydrideHCID 954944,4-Dimethyl-1-phenylpent-1-en-3-one

Product 1

HCID 54087959HCID 54087959, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6228DimethylformamideSolvent2×

Procedure

2,2-Dimethyl-5-phenylpent-4-ene-3-one (9.48 g) in carbon tetrachloride (60 ml) was treated dropwise with bromine (8.0 g). The solution was evaporated in a vacuum and the pale yellow residue of 4,5-dibromo-2,2-dimethyl-5-phenylpentan-3-one (12.6 g) collected. The dibromo compound so prepared (6.96 g) was dissolved in dry dimethylformamide (20 ml) and added dropwise to a mixture obtained by adding 1,2,4-triazole (2.76 g) to a suspension of sodium hydride (1.92 of 50% dispersion in mineral oil, washed free of oil with dry petrol) in dimethylformamide (10 ml). The resulting mixture was heated on a steambath for 15 minutes and poured into cold water (200 ml). The mixture was extracted with ether and the ether extracts dried and evaporated to give a pale yellow oil. This oil crystallised from petrol to give 2,2-dimethyl-5-phenyl-5-(1,2,4-triazol-1-yl)pent-4-en-3-one (compound no. 1 of Table I) having a melting point of 70°- 73° C.

Workup

  1. customThe solution was evaporated in a vacuum
  2. customthe pale yellow residue of 4,5-dibromo-2,2-dimethyl-5-phenylpentan-3-one (12.6 g) collected
  3. customThe dibromo compound so prepared (6.96 g)
  4. additionadded dropwise to a mixture
  5. customobtained
  6. temperatureThe resulting mixture was heated on a steambath for 15 minutes
  7. extractionThe mixture was extracted with ether
  8. dry with materialthe ether extracts dried
  9. customevaporated
  10. customto give a pale yellow oil
  11. customThis oil crystallised from petrol

Sources & evidence

ORD record
ord-dd6193f4059a410c947538443c5150f5
Source dataset
uspto-grants-1980_11
Patent number
US04235620

Reaction notes

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