Hydrochloric Acid → Phenyl 1-(N,N-Diethylcarbamoyl)-1,2,4-Triazole-3-Sulfonate

HRID 248853Notes

Reaction equation

HRID 248853 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([S:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:8])=[O:7])=[N:2]1.[CH2:16]([N:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])[CH3:17].Cl>N1C=CC=CC=1>[CH2:16]([N:18]([CH2:22][CH3:23])[C:19]([N:1]1[CH:5]=[N:4][C:3]([S:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:7])=[O:8])=[N:2]1)=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6916Diethylcarbamoyl chlorideHCID 178527608Phenyl 1,2,4-triazole-3sulfonate

Product 1

HCID 19762020Phenyl 1-(N,N-Diethylcarbamoyl)-1,2,4-Triazole-3-Sulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a flask was added 9.76 g of phenyl 1,2,4-triazole-3sulfonate and 40 ml of dry pyridine. The mixture was stirred under nitrogen until a solution became apparent. Diethylcarbamoyl chloride, 5.6 ml, was then added and the resulting mixture stirred under nitrogen at room temperature for 16 hours. The mixture was then poured into 100 ml of 2N hydrochloric acid and extracted twice with 100 ml portions of ethyl acetate. The ethyl acetate solution was dried using sodium sulfate, filtered and concentrated to yield 11.12 g of the desired product as a white solid.

Workup

  1. stirringthe resulting mixture stirred under nitrogen at room temperature for 16 hours
  2. extractionextracted twice with 100 ml portions of ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb3152f64df9448e939ed0ab953998f5
Source dataset
uspto-grants-1993_05
Patent number
US05211739

Reaction notes

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