Phenol → Phenyl 1,2,4-triazole-3sulfonate

HRID 248852Notes

Reaction equation

HRID 248852 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([S:6](Cl)(=[O:8])=[O:7])=[N:2]1.O1CCCC1.S(Cl)(Cl)(=O)=O.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(N(CC)CC)C>[NH:1]1[CH:5]=[N:4][C:3]([S:6]([O:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:8])=[O:7])=[N:2]1

Participants

6

Reactant 4

HCID 996PhenolHCID 8028TetrahydrofuranHCID 24648Sulfuryl chlorideHCID 178527437HCID 178527437, compound

Product 1

HCID 178527608Phenyl 1,2,4-triazole-3sulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a flask was added 10 g of thoroughly dried 1,2,4-triazole-3-sulfonyl chloride and 150 ml of tetrahydrofuran. The resulting mixture was stirred under nitrogen until most of the sulfonyl chloride dissolved. Phenol, 6.2 g, was then added at room temperature followed by the slow addition of 9 ml of triethyl amine. A precipitate became apparent and the resulting mixture was stirred for an additional 16 hours. The tetrahydrofuran was evaporated from the mixture and the residue washed with 200 ml of water followed by extraction with 200 ml of ethyl acetate. The ethyl acetate solution was dried using sodium sulfate, filtered and concentrated to yield 10.77 g of the desired intermediate as a white solid.

Workup

  1. dissolutiondissolved
  2. customThe tetrahydrofuran was evaporated from the mixture
  3. washthe residue washed with 200 ml of water
  4. extractionfollowed by extraction with 200 ml of ethyl acetate
  5. dry with materialThe ethyl acetate solution was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9ac885b41d91414393b9b2ee4fefec79
Source dataset
uspto-grants-1993_05
Patent number
US05211739

Reaction notes

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