Hexane → 4-phenyl-1H-1,2,3-triazole

HRID 1764079Notes

Reaction equation

HRID 1764079 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si]([N:13]=[N+:14]=[N-:15])(C)(C)C.CCCCCC>CCOCC>[C:1]1([C:7]2[N:13]=[N:14][NH:15][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 10821PhenylacetyleneHCID 78378Azidotrimethylsilane

Product 1

HCID 1784201274-phenyl-1H-1,2,3-triazoleYield 76.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
150 °C

Procedure

##STR9## Phenylethyne (12.0 g) and Me3SiN3 (7.8 g) were sealed into a heavy-walled glass reactor at -70° C. and 0.6 mm Hg. The mixture was heated at 150° C. for 10 hrs., cooled, and dissolved in Et2O. The Et2O was treated exactly as in Example 2, reduced to 100 ml total volume, a little hexane added and chilled in a refrigerator overnight. Filtration gave 7.5 g (76%) white crystals mp 146.9-149.0.

Workup

  1. temperature, cooled
  2. temperaturechilled in a refrigerator overnight
  3. filtrationFiltration

Sources & evidence

ORD record
ord-5a5dc2fb2cda4cd2bb2d3c6eeab48b27
Source dataset
uspto-grants-1978_09
Patent number
US04115288

Reaction notes

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