Chlorosulfonic acid → Thieno[2,3-b]pyridine-3-sulfonyl chloride

HRID 849507

Reaction equation

HRID 849507 reaction equation
[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([O-])(O)=O.[Na+].[Cl:15][S:16](O)(=[O:18])=[O:17]>>[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([S:16]([Cl:15])(=[O:18])=[O:17])=[CH:2]1

Participants

4

Reactant 3

HCID 24638Chlorosulfonic acidHCID 289928Thieno(2,3-b)pyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 18614041Thieno[2,3-b]pyridine-3-sulfonyl chloride

Conditions

Temperature
100 °C

Procedure

A solution of thieno[2,3-b]pyridine (0.70 g, 5.2 mmoles), prepared as described in Example 1(A), in chlorosulfonic acid, (7 ml) was heated to 100° C. for 15 minutes, then cooled to ambient temperature and added to ice (100 ml). The pH of the aqueous phase as adjusted to 8 with sat. NaHCO3, then extracted with CHCl3 (2×125 ml). The organic phase was dried (MgSO4), filtered and concentrated to collect 0.95 g (78%) of the title compound as a tan solid.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with CHCl3 (2×125 ml)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto collect 0.95 g (78%) of the title compound as a tan solid

Sources & evidence

ORD record
ord-09aca8f0d605409f8a1f64e8abed4ad1
Source dataset
uspto-grants-2000_01
Patent number
US06013655

Linked notes

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