Diethyl Sulfate → HCID 15491018, compound

HRID 392782Notes

Reaction equation

HRID 392782 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[N:11][C:10]([C:23]([F:26])([F:25])[F:24])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[K+].[CH2:29](OS(OCC)(=O)=O)[CH3:30].[NH4+].[OH-]>O.CN(C=O)C>[CH2:29]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=3)=[N:11][C:10]([C:23]([F:24])([F:25])[F:26])=[N:9]2)=[CH:6][CH:7]=1)[CH3:30]

Participants

7

Reactant 4

HCID 6163Diethyl SulfateHCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 15491017HCID 15491017, compound

Product 1

HCID 15491018HCID 15491018, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-hydroxy-phenyl)-5-(4-methylsulfonyl-phenyl)-3-trifluoromethyl-1H-1,2,4-triazole (4 g, 10.4 mmol), KOH (1.5 g, 26.8 mmol) and DMF (40 ml) was stirred at room temperature for 1 h. Then diethylsulfate (1.6 ml, 12.2 mmol) was added, the reaction mixture stirred at room temperature for 13 h, NH4OH (20 ml) added and the mixture poured into water (1 l). The precipitate was filtered, washed several times with water and dried. Recrystallization from ethanol yielded a white solid (3.7 g, 88%).

Workup

  1. stirringthe reaction mixture stirred at room temperature for 13 h
  2. filtrationThe precipitate was filtered
  3. washwashed several times with water
  4. customdried
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-2c363c827321407cb087d2d24f2f71cc
Source dataset
uspto-grants-2004_10
Patent number
US06803380B1

Reaction notes

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