Diphenylacetylene → HCID 178420171, compound

HRID 1605000Notes

Reaction equation

HRID 1605000 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N:19]=[N+:20]=[N-:21])(C)C>>[C:1]1([C:7]2[N:19]=[N:20][NH:21][C:8]=2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 10390DiphenylacetyleneHCID 78378Azidotrimethylsilane

Product 1

HCID 178420171HCID 178420171, compoundYield 27.4%

Conditions

Temperature
150 °C

Procedure

A mixture of 50 g (0.28 moles) of diphenylacetylene and 33 g (0.28 moles) of trimethylsilylazide was heated at 150°C for several days. The cooled reaction mixture was extracted with hot dlute NaOH. This was washed with toluene while still warm, cooled, and acidified. The precipitate was recrystallized from toluene to give 17 g of 4,5-diphenyl-1,2,3(1H)-triazole, m.p. 131°C.

Workup

  1. customThe cooled reaction mixture
  2. extractionwas extracted with hot dlute NaOH
  3. washThis was washed with toluene
  4. temperaturewhile still warm
  5. temperaturecooled
  6. customThe precipitate was recrystallized from toluene

Sources & evidence

ORD record
ord-bd8910ad6a00405090f38af83c90a636
Source dataset
uspto-grants-1976_04
Patent number
US03948930

Reaction notes

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