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

HRID 705021

반응식

HRID 705021 반응식
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

참가 물질

10

반응물 6

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

생성물 1

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

시약·촉매·용매 3

HCID 24463Copper sulfate pentahydrate촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d21137ace2c34b2e9e3bc8ae006fda59
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173401B2

연결된 노트

불러오는 중…