Dichloromethane → 5-Pyridin-3-yl-thiophene-2-sulfonyl chloride

HRID 1636790

Reaction equation

HRID 1636790 reaction equation
[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

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 5951453-(2-Thienyl)pyridineHCID 178418339Butyllithium

Product 1

HCID 106589765-Pyridin-3-yl-thiophene-2-sulfonyl chlorideYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-thiophen-2-yl-pyridine (0.35 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 minutes, SO2 gas is bubbled through the solution for 30 minutes. 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 minutes and then a small amount of methylene chloride is added and the mixture is stirred for another 30 minutes. 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.

Workup

  1. customSO2 gas is bubbled through the solution for 30 minutes
  2. stirringstirred overnight
  3. concentrationThe solution is concentrated to dryness
  4. stirringthe reaction mixture is stirred for 30 minutes
  5. stirringthe mixture is stirred for another 30 minutes
  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

Sources & evidence

ORD record
ord-662596773ac24d7da58b54eed794752d
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Linked notes

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