Methanol → HCID 20551093, compound

HRID 1447080Notes

Reaction equation

HRID 1447080 reaction equation
[C:1]1(=[CH:7][CH:8]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:9]([OH:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Cl.CO>O1CCOCC1>[C:1]1(=[CH:7][CH:8]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:9]([O:14][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[Cl:22])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 20551089HCID 20551089, compound

Product 1

HCID 20551093HCID 20551093, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of 13.1 g (0.15 mol) of 1-cyclohexylidene-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pentan-3-ol (Example 2) in 50 ml of dioxane was added dropwise to a suspension of 2.0 g of 80% strength sodium hydride in 50 ml of dioxane and the mixture was then warmed to 65° C. for 45 minutes. After cooling, 10.0 g (0.06 mol) of 2-chlorobenzyl chloride were added dropwise and the mixture was heated under reflux overnight. 5 ml of methanol were then added and the reaction was concentrated. The residue was taken up in methylene chloride and the methylene chloride mixture was washed several times with water. The organic phase was dried over sodium sulphate, concentrated and finally degassed under a high vacuum. 14.2 g (72% of theory) of 1-cyclohexylidene-3-(2-chlorobenzyloxy)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pentane were obtained as a yellowish oil with a refractive index of nD20 =1.5349.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux overnight
  4. concentrationthe reaction was concentrated
  5. washthe methylene chloride mixture was washed several times with water
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. concentrationconcentrated
  8. customfinally degassed under a high vacuum

Sources & evidence

ORD record
ord-f583270830314c638ddb47d7679e0db6
Source dataset
uspto-grants-1982_02
Patent number
US04315764

Reaction notes

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