Pentamethyldiethylenetriamine → HCID 90410677, compound

HRID 1476682Notes

Reaction equation

HRID 1476682 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[S:6][CH:7]=[CH:8][CH:9]=1.[C:12]1([N:18]=[N+:19]=[N-:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CN(C)CCN(C)CCN(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cu]I>[C:12]1([N:18]2[CH:3]=[C:4]([C:5]3[S:6][CH:7]=[CH:8][CH:9]=3)[N:20]=[N:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 18196PentamethyldiethylenetriamineHCID 69319AzidobenzeneHCID 5968702-[(Trimethylsilyl)ethynyl]thiopheneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 90410677HCID 90410677, compoundYield 47,533.301%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of trimethyl(thiophen-2-ylethynyl)silane (50 mg, 0.2777 mmol), phenyl azide (0.5 M solution, 1.1 ml, 0.555 mmol), and CuI (52.87 mg, 0.2777 mmol) in THF (1 ml) was added 1,1,4,7,7-pentamethyldiethlenetriamine (0.116 ml, 0.555 mmol) and 1M TBAF.3H2O (0.554 ml, 0.554 mmol). After stirring the reaction mixture for 20 hours at room temperature, it was quenched with saturated ammonium chloride solution and was extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate and evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using 5% ethyl acetate in hexane as eluant to yield 1-phenyl-4-(thiophen-2-yl)-1H-1,2,3-triazole (30 mg, 0.132 mol, yield 47.61%) with an HPLC purity of 97.64%. LC-MS [M+H] 228.2 (C12H9N3S+H, expected 228.05). The 1H-NMR spectra was in accordance with the chemical structure.

Workup

  1. customit was quenched with saturated ammonium chloride solution
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe crude material was purified by column chromatography (100-200 mesh silica gel)

Sources & evidence

ORD record
ord-4c32fee4ccf84219a95c4ae2adb397f5
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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