Water → HCID 19872277, compound

HRID 477748Notes

Reaction equation

HRID 477748 reaction equation
[CH2:1]([S:8][C:9]1[N:13]=[C:12]([OH:14])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.[CH3:26][O+](C)C.O>ClCCl>[CH2:1]([S:8][C:9]1[N:13]=[C:12]([O:14][CH3:26])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 178518539HCID 178518539, compound

Product 1

HCID 19872277HCID 19872277, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Benzylthio-5-hydroxy-1-phenyl-1,2,4-triazole (15 g) in dichloromethane (60 ml) was treated with trimethyloxonium tetrafluoroborate (15.7 g) and allowed to stand for 18 hours at room temperature. The reaction mixture was poured into water (200 ml) and the aqueous layer was washed with dichloromethane (2×100 ml). The dried organic layer was evaporated and then purified by column chromatography (silica/petroleum ether:ether), to give 8.1 g of the desired product.

Workup

  1. washthe aqueous layer was washed with dichloromethane (2×100 ml)
  2. customThe dried organic layer was evaporated
  3. custompurified by column chromatography (silica/petroleum ether:ether)

Sources & evidence

ORD record
ord-0add69fccb2c4325b368ced7bf65ca27
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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