반응 #1563866

반응 방정식

NaN3

2-ethynylthiophene

1-chloro-4-iodobenzene

L-proline

Na2CO3

sodium ascorbate

→

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

수율 5.5%

용매

DMSO H2O

반응 조건

후처리

1. 1
   기타the vessel was sealed
2. 2
   추출extracted with ethyl acetate
3. 3
   기타The organic layer was separated
4. 4
   세척washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated under vacuum
7. 7
   기타The crude product was then purified by silica column (100-200)

실험 절차

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.

출처