Triethylamine → HCID 57379103, compound

HRID 1429289Notes

Reaction equation

HRID 1429289 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 Pfaltz & Bauer, Inc., 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. custom, or can 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-90670d5cdd3149518e66129f54f64f89
Source dataset
uspto-grants-2015_01
Patent number
US08940274B2

Reaction notes

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