Thionyl Chloride → 5-(2-Pyridinyl)-2-thiophenecarbonyl chloride

HRID 857903Notes

Reaction equation

HRID 857903 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=1.S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:11][C:10]([C:12]([Cl:17])=[O:14])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 7364825-(Pyridin-2-yl)thiophene-2-carboxylic acid

Product 1

HCID 27761995-(2-Pyridinyl)-2-thiophenecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 5-(pyrid-2-yl)thiophene-2-carboxylic acid (48 mg) in dry toluene (10 mL) was treated with thionyl chloride (269 μL). After stirring at 100° C. for 2.5 hours the reaction mixture was allowed to cool to room temperature and then evaporated. The residue was azeotroped with toluene to give the title compound (61 mg), which was used without further purification.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated
  3. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-55f3978291be48ed873c6e58e5b102a5
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

Loading…