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

HRID 1476684

反応式

HRID 1476684 の反応式
[C:1]([C:3]1[S: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+]>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[S:4][CH:5]=[CH:6][CH:7]=3)[N:45]=[N:44]2)=[CH:11][CH:10]=1

参加物

8

反応物 6

HCID 10340Sodium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 33557Sodium AzideHCID 145742L-ProlineHCID 52462582-EthynylthiopheneHCID 23667548Sodium Ascorbate

生成物 1

HCID 863036561-(4-chloro-phenyl)-4-(thiophen-2-yl)-1H-1,2,3-triazole収率 5.5%

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 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.

後処理

  1. customthe vessel was sealed
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe crude product was then purified by silica column (100-200)

出典と根拠

ORDレコード
ord-76a6409c3fb74f2d883e987204d32a0e
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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