Sodium Carbonate → 1-(4-chlorophenyl)-4-(furan-2-yl)-1H-1,2,3-triazole

HRID 705006

Reaction equation

[C:1]([C:3]1[O: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+].[OH-].[NH4+]>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[O:4][CH:5]=[CH:6][CH:7]=3)[N:45]=[N:44]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A sealed tube was charged sequentially with 2-ethynylfuran (153 mg, 1.663 mmol), 1-chloro-4-iodobenzene (395 mg, 1.663 mmol), L-proline (38.2 mg, 0.332 mmol), Na2CO3 (35 mg, 0.332 mmol), sodium ascorbate (66 mg, 0.332 mmol), DMSO-H2O (9:1; 7 ml), NaN3 (130 mg, 1.99 mmol) and CuSO4.5H2O (415 mg, 1.663 mmol). The tube was sealed and stirred at 65° C. for 16 hours. The reaction mixture was poured onto cold ammonium hydroxide solution, and the mixture was extracted with ethyl acetate (3×30 ml). The combined organic layers were washed with brine solution (30 ml), dried over sodium sulfate and evaporated to yield the crude material, which was purified by column chromatography with 20% ethyl acetate/hexane yielding 1-(4-chlorophenyl)-4-(furan-2-yl)-1H-1,2,3-triazole (20 mg, yield 4.9%) as a pale yellow solid. The HPLC purity was 98.02%. LC-MS [M+H] 246 (C12H8ClN3O+H, expected 246.04). The 1H-NMR spectra was in accordance with the chemical structure.

Workup

customThe tube was sealed
extractionthe mixture was extracted with ethyl acetate (3×30 ml)
washThe combined organic layers were washed with brine solution (30 ml)
dry with materialdried over sodium sulfate
customevaporated
customto yield the crude material, which
customwas purified by column chromatography with 20% ethyl acetate/hexane

Sources & evidence

ORD record: ord-cb57fe7a069743b1ba7f72f81f98dfb7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173401B2

Linked notes

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