Diphenylacetylene → HCID 178420171, compound

HRID 1605002Notes

Reaction equation

HRID 1605002 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-0e7cfba51a4e479aae00ed10f2a3366f
Source dataset
uspto-grants-1976_04
Patent number
US03948932

Reaction notes

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