Thionyl Chloride → 6-(3-Thienyl)-2-pyridinesulfonyl chloride

HRID 130405Notes

Reaction equation

HRID 130405 reaction equation
[Na+].[S:2]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11]([S:13]([O-:16])(=O)=[O:14])[CH:10]=[CH:9][CH:8]=2)=[CH:3]1.S(Cl)([Cl:19])=O>CN(C)C=O>[S:2]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11]([S:13]([Cl:19])(=[O:16])=[O:14])[CH:10]=[CH:9][CH:8]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59007067HCID 59007067, compound

Product 1

HCID 590070916-(3-Thienyl)-2-pyridinesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of 6-(3-thienyl)-2-pyridinesulfonic acid sodium salt (D9) and N,N-dimethylformamide (1 drop) in thionyl chloride (2 ml) was heated at 70° C. for 2 hours. After cooling to room temperature the solution was concentrated in vacuo and the residue co-evaporated with toluene (×2). The residue was triturated with diethyl ether to afford the title product (D10).

Workup

  1. temperatureAfter cooling to room temperature the solution
  2. concentrationwas concentrated in vacuo
  3. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-6e4c2f59a9c2482a8e1cde73eb428536
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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