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

HRID 705021

反応式

HRID 705021 の反応式
Br[C:2]1[O:3][CH:4]=[CH:5][CH:6]=1.[C:7]1([C:13]#[CH:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[N-:29]=[N+:30]=[N-:31].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O.CS(C)=O>[O:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[N:29]1[CH:14]=[C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:31]=[N:30]1

参加物

10

反応物 6

HCID 10340Sodium CarbonateHCID 10821PhenylacetyleneHCID 33557Sodium AzideHCID 145742L-ProlineHCID 2776190Furan, 2-bromo-HCID 23667548Sodium Ascorbate

生成物 1

HCID 904121181-(furan-2-yl)-4-phenyl-1H-1,2,3-triazole収率 5%

試薬・触媒・溶媒 3

HCID 24463Copper sulfate pentahydrate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

A stirred solution of 2-bromofuran (500 mg, 3.40 mmol) and phenyl acetylene (347 mg, 3.39 mmol) in a mixture of solvents (9:1 DMSO:H2O, 4 mL) was prepared in a Pierce reaction vessel. L-proline (78 mg, 0.68 mmol), sodium carbonate (72 mg, 0.68 mmol), sodium azide (265 mg, 4.07 mmol), copper sulfate, pentahydrate (43 mg, 0.17 mmol), and sodium ascorbate (67 mg, 0.34 mmol), respectively, were then added to the vessel. The reaction vessel was capped and the mixture was heated at 65° C. for 18 hours. The reaction mass was poured into 50 mL of ice-water, stirred for 10 minutes, and extracted with ethyl acetate (3×30 mL). The combined organic extract was then washed with brine (50 mL), dried over Na2SO4, and evaporated under vacuum. The resulting crude compound was auto purified through preparative HPLC to yield the desired 1-(furan-2-yl)-4-phenyl-1H-1,2,3-triazole (36 mg, 5%) as a light yellow solid. The melting point of the final product was determined to be 99-101° C. The HPLC purity of the final product was 95.34%. LC-MS [M+1]212 (C12H9N3O+H expected 212.07). The 1H-NMR spectra was in accordance with the chemical structure.

後処理

  1. customwas prepared in a Pierce reaction vessel
  2. customThe reaction vessel was capped
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. extractionThe combined organic extract
  5. washwas then washed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated under vacuum
  8. custompurified through preparative HPLC

出典と根拠

ORDレコード
ord-d21137ace2c34b2e9e3bc8ae006fda59
出典データセット
uspto-grants-2015_11
特許番号
US09173401B2

関連ノート

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