Diphenylacetylene → HCID 178420171, compound

HRID 1287653

Reaction equation

HRID 1287653 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 dilute 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 dilute 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-eecb2c9d46de49d48d1ccae59357b559
Source dataset
uspto-grants-1976_10
Patent number
US03985765

Linked notes

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