二氯甲烷 → 5-Pyridin-3-yl-thiophene-2-sulfonyl chloride

HRID 2772

反应方程式

HRID 2772 反应方程式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[Li]CCCC.[S:17](Cl)([Cl:20])(=[O:19])=[O:18].C(Cl)Cl>C1COCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:2]2[S:1][C:5]([S:17]([Cl:20])(=[O:19])=[O:18])=[CH:4][CH:3]=2)[CH:7]=1

参与物

6

反应物 4

HCID 6344二氯甲烷HCID 24648磺酰氯HCID 5951453-(2-噻吩基)吡啶HCID 178418339正丁基锂

产物 1

HCID 106589765-Pyridin-3-yl-thiophene-2-sulfonyl chloride收率 79.1%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

To a solution of 3-thiophen-2-yl-pyridine (0.355 g, 2.20 mmol) in 15 mL of THF at -78° C. is added n-BuLi (1.44 mL of a 1.6M solution in hexanes, 2.31 mmol). After stirring for 15 min, SO2 gas is bubbled through the solution for 30 min. The solution is then allowed to warm to room temperature and stirred overnight. The solution is concentrated to dryness and the resulting solid is suspended in 20 mL of hexane. Sulfuryl chloride (0.185 mL, 2.31 mmol) is added and the reaction mixture is stirred for 30 min then a small amount of methylene chloride is added and the mixture is stirred for another 30 min. The mixture is then concentrated to dryness and diluted with ethyl acetate and washed with saturated NaHCO3 (aq), water and brine. The organic layer is dried over MgSO4, filtered and concentrated to give a brown solid as the title product (0.452 g, 1.74 mmol) which is used in the subsequent step without further purification.

后处理

  1. customSO2 gas is bubbled through the solution for 30 min
  2. stirringstirred overnight
  3. concentrationThe solution is concentrated to dryness
  4. stirringthe reaction mixture is stirred for 30 min
  5. stirringthe mixture is stirred for another 30 min
  6. concentrationThe mixture is then concentrated to dryness
  7. additiondiluted with ethyl acetate
  8. washwashed with saturated NaHCO3 (aq), water and brine
  9. dry with materialThe organic layer is dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

来源与证据

ORD记录
ord-385105c7ada24b3c981f877c5e6c950f
来源数据集
uspto-grants-1998_03
专利号
US05731315

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