2-Thiophenesulfonyl chloride → HCID 3078271, compound

HRID 1164837Notes

Reaction equation

HRID 1164837 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[CH2:10]([N:17]1[CH2:24][CH:23]2[C:25]([CH3:27])([CH3:26])[CH:19]([CH2:20][NH:21][CH2:22]2)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl>[CH2:10]([N:17]1[CH2:18][CH:19]2[C:25]([CH3:27])([CH3:26])[CH:23]([CH2:22][N:21]([S:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)(=[O:8])=[O:7])[CH2:20]2)[CH2:24]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 14369013HCID 14369013, compound

Product 1

HCID 3078271HCID 3078271, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.87 g (=0.015 mol) thiophene-2-sulfonyl chloride in 20 ml dichloromethane was added dropwise with ice cooling to a solution of 3.5 g (=0.014 mol) 7-benzyl-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane (=substance No. C8 in the following Table C) in 40 ml dichloromethane. Then the ice bath was removed and the reaction mixture stirred further for 3 hours at room temperature. The reaction mixture was then made alkaline by adding aqueous sodium hydroxide solution, the aqueous phase was separated and extracted twice with dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and the solvent was evaporated. 4.0 g of the title compound (base) were thereby obtained as an oil.

Workup

  1. customThen the ice bath was removed
  2. additionby adding aqueous sodium hydroxide solution
  3. customthe aqueous phase was separated
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-47e5f15a3fd04cf386a5bf854d7a90fb
Source dataset
uspto-grants-1990_03
Patent number
US04906640

Reaction notes

Loading…