Acetyl chloride → (5-Methyl-2-phenyl-2H-1,2,3-triazol-4-yl)methanol

HRID 478333Notes

Reaction equation

HRID 478333 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[N+:5]([O-])[N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.C(Cl)(=[O:17])C.[OH-].[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:1][C:2]1[C:6]([CH2:7][OH:17])=[N:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 14798Sodium HydroxideHCID 12921197HCID 12921197, compound

Product 1

HCID 563195(5-Methyl-2-phenyl-2H-1,2,3-triazol-4-yl)methanolYield 80.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent5×HCID 8471TriethylamineSolvent2×

Conditions

Temperature
80 °C

Procedure

7.1 g of 4,5-dimethyl-2-phenyl-1,2,3-triazol-1-oxide was dissolved in 25 ml of toluene, and heated to 80° C. 4.8 g of acetyl chloride diluted with 13 ml of toluene and 9.1 ml of triethylamine diluted with 13 ml of toluene were simultaneouly added dropwise thereto, keeping the temperature below 85° C. After stirring for 1 hour at 80° C., 2.5 ml of acetyl chloride diluted with 5 ml of toluene and 4.5 ml of triethylamine diluted with 5 ml of toluene were simultaneously added. After stirring for 1 hour at 80° C., the solution was left overnight at room temperature. 7 ml of 30% aqueous solution of sodium hydroxide was added, then toluene and triethylamine were distilled off under reduced pressure. 5 ml of ethanol and 30% aqueous solution of sodium hydroxide were added, and refluxed with heating for 1 hour. After ethanol was distilled off under reduced pressure, 50 ml of 10% saline solution was added, and left for some time at room temperature. The deposited crystals was dissolved in ethyl acetate, washed with water and a saturated salt solution, then dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified through silica gel column chromatography (hexan/ethyl acetate=1/2), then washed with hexan/diisopropyl ether (=10/1) to obtain 5.7 g of the aimed compound.

Workup

  1. additionwere simultaneouly added dropwise
  2. customthe temperature below 85° C
  3. additionwere simultaneously added
  4. stirringAfter stirring for 1 hour at 80° C.
  5. waitthe solution was left overnight at room temperature
  6. distillationtoluene and triethylamine were distilled off under reduced pressure
  7. addition5 ml of ethanol and 30% aqueous solution of sodium hydroxide were added
  8. temperaturerefluxed
  9. temperaturewith heating for 1 hour
  10. distillationAfter ethanol was distilled off under reduced pressure, 50 ml of 10% saline solution
  11. additionwas added
  12. waitleft for some time at room temperature
  13. dissolutionThe deposited crystals was dissolved in ethyl acetate
  14. washwashed with water
  15. dry with materiala saturated salt solution, then dried over anhydrous sodium sulfate
  16. distillationAfter the solvent was distilled off
  17. customthe residue was purified through silica gel column chromatography (hexan/ethyl acetate=1/2)
  18. washwashed with hexan/diisopropyl ether (=10/1)

Sources & evidence

ORD record
ord-c691d93d12ec446a887cd2ea01e72f3f
Source dataset
uspto-grants-2003_11
Patent number
US06642234B1

Reaction notes

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