4-tert-Butylphenol → HCID 18998871, compound

HRID 2260655Notes

Reaction equation

HRID 2260655 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[C:14]([C:18]1[CH:30]=[CH:29][C:21]([O:22][C:23]2[C:27](Cl)=[N:26][S:25][N:24]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O.O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([O:13][C:27]2[C:23]([O:22][C:21]3[CH:29]=[CH:30][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=3)=[N:24][S:25][N:26]=2)=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 73934-tert-ButylphenolHCID 24758Sodium hydrideHCID 18998870HCID 18998870, compound

Product 1

HCID 18998871HCID 18998871, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension formed by suspending 0.16 g of sodium hydride (60%) in N,N-dimethylformamide was added 0.6 g of 4-t-butylphenol and after stirring the mixture for one hour at 60° C., 0.81 g of 3-(4-t-butylphenoxy)-4-chloro-1,2,5-thiadiazole was added to the mixture followed by stirring for 12 hours at 100° C. After allowing to cool, the reaction mixture was poured in water and extracted with ether. The ether layer collected was washed twice each time with a diluted aqueous sodium hydroxide solution, water, and then a saturated aqueous sodium chloride solution. The ether layer thus washed was dried with anhydrous magnesium sulfate, concentrated, and purified by silica column chromatography to provide 0.84 g of 3,4-bis(4-t-butylphenoxy)-1,2,5-thiadiazole.

Workup

  1. customTo a suspension formed
  2. stirringby stirring for 12 hours at 100° C
  3. temperatureto cool
  4. extractionextracted with ether
  5. customThe ether layer collected
  6. washwas washed twice each time with a diluted aqueous sodium hydroxide solution, water
  7. washThe ether layer thus washed
  8. dry with materialwas dried with anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. custompurified by silica column chromatography

Sources & evidence

ORD record
ord-bdec988b07454d708b26e974398ec4aa
Source dataset
uspto-grants-1995_12
Patent number
US05478849

Reaction notes

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