Sodium Carbonate → 1-(4-chloro-phenyl)-4-(thiophen-2-yl)-1H-1,2,3-triazole

HRID 1476684

Reaktionsgleichung

[C:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)#[CH:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1.N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[Na+].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[N-:43]=[N+:44]=[N-:45].[Na+]>CS(C)=O.O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:43]2[CH:2]=[C:1]([C:3]3[S:4][CH:5]=[CH:6][CH:7]=3)[N:45]=[N:44]2)=[CH:11][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A sealed tube was sequentially charged with 2-ethynylthiophene (250 mg, 2.31 mol), 1-chloro-4-iodobenzene (551 mg, 2.31 mmol, 1.0 eq.), L-proline (53 mg, 0.462 mmol, 0.2 eq.), Na2CO3 (50 mg, 0.462 mmol, 0.2 eq.), sodium ascorbate (91 mg, 0.462 mmol, 0.2 eq.), and 4 mL of DMSO:H2O (9:1). Then NaN3 (180 mg 2.77 mmol, 1.2 eq.) and CuSO4.5H2O (58 mg. 0.231 mmol, 0.1 eq.) were added, and the vessel was sealed. The suspension was stirred at 65° C. for 16 hours. The reaction mixture was then poured into ice-water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4, and concentrated under vacuum. The crude product was then purified by silica column (100-200) using 15-20% ethyl acetate/hexanes to yield 1-(4-chloro-phenyl)-4-(thiophen-2-yl)-1H-1,2,3-triazole as a brown solid compound (34 mg, 0.13 mmol yield 5.5%). LC-MS [M+H] 261.8 (C12H8ClN3S+H, expected 262.01). The 1H-NMR spectra was in accordance with the chemical structure.

Aufarbeitung

customthe vessel was sealed
extractionextracted with ethyl acetate
customThe organic layer was separated
washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customThe crude product was then purified by silica column (100-200)

Quellen und Nachweise

ORD-Eintrag: ord-76a6409c3fb74f2d883e987204d32a0e
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09402397B2

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