Iodine → HCID 13259988, compound

HRID 483114Notes

Reaction equation

HRID 483114 reaction equation
[Al].II.[CH2:4](Br)[C:5]#[CH:6].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)[C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=1.[Cl-].[NH4+]>O1CCCC1.[Hg](Cl)Cl>[C:18]([C:17]([OH:22])([CH:16]([N:23]1[CH:27]=[N:26][CH:25]=[N:24]1)[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=1)[CH2:6][C:5]#[CH:4])([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 5

HCID 807IodineHCID 7842Propargyl bromideHCID 25517Ammonium ChlorideHCID 5359268AluminumHCID 129255611-(4-Chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-3-pentanone

Product 1

HCID 13259988HCID 13259988, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

3.7 g of aluminum (in the form of flakes), a pinch of mercury(II) chloride and an iodine crystal are stirred with 20 ml of absolute tetrahydrofuran for 12 hours. 24 g (0.2 mol) of propargyl bromide, dissolved in 25 ml of tetrahydrofuran, are then added dropwise at 50° to 60° C. The mixture is stirred for a further 30 minutes at 60° C. and cooled to -60° C., and 29.2 g (0.1 mol) of 5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-pentan-3-one in 100 ml of tetrahydrofuran are slowly added dropwise. Thereafter, the reaction mixture is stirred for a further hour at 0° C. and for 2 hours at 20° C., 50 ml of saturated, aqueous ammonium chloride solution are added, while cooling, the mixture is filtered and the filtrate is evaporated down. The remaining crystalline residue is digested with water and recrystallized from 520 ml of cyclohexane. 24.6 g (74.2% of theory) of 4-tert.-butyl-6-(4-chlorophenyl)-5-(1,2,4 -triazol-1-yl)-hex-1-in-4-ol of melting point 121° C. are obtained.

Workup

  1. additionare then added dropwise at 50° to 60° C
  2. temperaturecooled to -60° C.
  3. stirringThereafter, the reaction mixture is stirred for a further hour at 0° C. and for 2 hours at 20° C.
  4. temperaturewhile cooling
  5. filtrationthe mixture is filtered
  6. customthe filtrate is evaporated down
  7. customrecrystallized from 520 ml of cyclohexane

Sources & evidence

ORD record
ord-0c7010a08de74e84b4f715a1f4184451
Source dataset
uspto-grants-1986_03
Patent number
US04578396

Reaction notes

Loading…