Triethylamine → HCID 57379103, compound

HRID 2280230Notes

Reaction equation

HRID 2280230 reaction equation
[C:1]1([N:7]=[N+:8]=[N-:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([Sn:14]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[C:15]#[CH:16])[CH2:11][CH2:12][CH3:13].C(N(CC)CC)C>C1COCC1.[Cu]I>[C:1]1([N:7]2[CH:16]=[C:15]([Sn:14]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69319Azidobenzene2×HCID 621176Ethynyltributyltin

Product 1

HCID 57379103HCID 57379103, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Phenylazide can be obtained from Sigma-Aldrich or can be synthesized by the method described in J. Biochem., 179, 397-405 (1979). A solution of tributylethynyl stannane (Sigma Aldrich; 400 mg, 1.27 mmol) in THF (4 mL) is treated with phenylazide (169 mg, 1.27 mmol), copper (I) iodide (90 mg, 0.47 mmol), and triethylamine (256 mg, 2.54 mmol) at room temperature over 48 h. The reaction is then filtered through celite to remove copper (I) iodide and chromatographed on silica in a gradient of 5-20% ethyl acetate in petrol. The second fraction is collected and concentrated in vacuo to give the 1-phenyl-4-(tributylstannyl)-1H [1,2,3]triazole as a colourless oil.

Workup

  1. customcan be synthesized by the method
  2. filtrationThe reaction is then filtered through celite
  3. customto remove copper (I) iodide
  4. customchromatographed on silica in a gradient of 5-20% ethyl acetate in petrol
  5. customThe second fraction is collected
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-502737c73de44065bf22f3a51bc859da
Source dataset
uspto-grants-2015_09
Patent number
US09138493B2

Reaction notes

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