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

HRID 1476683

反応式

HRID 1476683 の反応式
[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

参加物

9

反応物 7

HCID 10340Sodium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 140409Furan, 2-ethynyl-HCID 145742L-ProlineHCID 23667548Sodium Ascorbate

生成物 1

HCID 863035071-(4-chlorophenyl)-4-(furan-2-yl)-1H-1,2,3-triazole収率 4.9%

試薬・触媒・溶媒 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5e21d91017a446c9a43e1b14ba0fb3de
出典データセット
uspto-grants-2016_08
特許番号
US09402397B2

関連ノート

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