Aluminum → (2,4-Dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

HRID 1478500Notes

Reaction equation

HRID 1478500 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][CH:11]=2)[OH:9])=[C:5]([CH3:7])[N:6]=1.[Al]>O=[Mn]=O.O1CCOCC1>[CH3:1][C:2]1[S:3][C:4]([C:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][CH:11]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 2

HCID 5359268AluminumHCID 86715631(2,4-Dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 86715632(2,4-Dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a 500 mL flask containing (2,4-dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (10.5 g, 46.8 mmol, Intermediate 16: step a) was added 1,4-dioxane (400 mL) and the contents were warmed to form a homogeneous solution. Activated MnO2 (18 g, 207 mmol) was added and the dark brownish mixture was heated to reflux in an aluminum heating mantle under an atmosphere of N2. After 1.5 hours, the contents were filtered while still hot through Celite® and rinsed with warm THF. The resulting light orange solution was concentrated and passed through a silica gel column (25% acetone-DCM) to provide the title compound as a light orange solid.

Workup

  1. temperaturethe contents were warmed
  2. customto form a homogeneous solution
  3. temperaturethe dark brownish mixture was heated
  4. filtrationthe contents were filtered while still hot through Celite®
  5. washrinsed with warm THF
  6. concentrationThe resulting light orange solution was concentrated

Sources & evidence

ORD record
ord-5db7e6bc90d8493da77e76302c0b48ce
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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