1H-1,2,4-Triazole → HCID 178460846, compound

HRID 1601387Notes

Reaction equation

HRID 1601387 reaction equation
[CH3:1][C:2]([S:16][C@@H:17]1[CH2:22][O:21][C@@H:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:19][CH2:18]1)([CH3:15])[C:3]([C:5]1C=CC(C(F)(F)F)=CC=1)=[O:4].[I-].C[S+](C)(C)=O.[OH-].[K+].[NH:37]1[CH:41]=[N:40][CH:39]=[N:38]1>C(O)(C)(C)C.O.C(Cl)(Cl)Cl>[CH3:1][C:2]([S:16][C@@H:17]1[CH2:22][O:21][C@@H:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:19][CH2:18]1)([CH3:15])[CH:3]([OH:4])[CH2:5][N:37]1[CH:41]=[N:40][CH:39]=[N:38]1

Participants

8

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 14797Potassium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 178460845HCID 178460845, compound

Product 1

HCID 178460846HCID 178460846, compoundYield 104.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6386tert-ButanolSolvent

Procedure

680 mg (1.66 mmol) of 2-methyl-2-[(trans-2-phenyl-1,3-dioxan-5-yl)thio]-4'-(trifluoromethyl)propiophenone, 547 mg (2.49 mmol) of trimethylsulfoxonium iodide, 381 mg (6.79 mmol) of potassium hydroxide and 264 mg (3.82 mmol) of 1,2,4-triazole were heated with stirring in 5.7 ml of t-butanol at 80° C. for 6 hours. After cooling, the reaction mixture was distributed between chloroform and water and the chloroform layer was separated and dried, followed by evaporation of the solvent. The thus obtained oil was subjected to column chromatography using silica gel and eluted with a mixed solvent of ethyl acetate-hexane (1:1) to obtain 605 mg (yield: 74%) of the title compound as a foam.

Workup

  1. temperatureAfter cooling
  2. customthe chloroform layer was separated
  3. customdried
  4. customfollowed by evaporation of the solvent
  5. washeluted with a mixed solvent of ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-8309a0700bc84e69810baf0007459c3c
Source dataset
uspto-grants-1999_11
Patent number
US05977152

Reaction notes

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