1H-1,2,4-Triazole → HCID 23365302, compound

HRID 2107062Notes

Reaction equation

HRID 2107062 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:4][CH:3]=1.[I-].[CH3:18][S+](C)(C)=O.[OH-].[K+].[NH:25]1[CH:29]=[N:28][CH:27]=[N:26]1>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH2:18][N:25]2[CH:29]=[N:28][CH:27]=[N:26]2)([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[OH:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 14797Potassium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 22165700HCID 22165700, compound

Product 1

HCID 23365302HCID 23365302, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 1-(4-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-one (15 g), trimethylsulphoxonium iodide (17.5 g), potassium hydroxide (8.57 g), 1,2,4-triazole (5.48 g) and tert-butanol (150 ml) was heated under reflux for 5 h, then cooled overnight. The excess tert butanol was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic phase was separated, washed with water, dried, and evaporated to dryness to give a brown gum, which was purified by column chromatography on silica eluting with chloroform/methanol, 97:3 by volume, to give a high melting polymorph of 2-(4-chlorophenyl)-1,1-di(1,2,4-triazol-1-ylmethyl)ethanol, mp 170°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. temperaturecooled overnight
  4. customThe excess tert butanol was evaporated under reduced pressure
  5. customthe residue was partitioned between ethyl acetate and water
  6. customThe organic phase was separated
  7. washwashed with water
  8. customdried
  9. customevaporated to dryness
  10. customto give a brown gum, which
  11. customwas purified by column chromatography on silica eluting with chloroform/methanol, 97:3 by volume

Sources & evidence

ORD record
ord-c799460117f14989894c950aab8910b2
Source dataset
uspto-grants-1990_06
Patent number
US04933357

Reaction notes

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