Dimethylformamide → 2-Chloro-1-(2-thienyl)-2-oxo-1-ethanone

HRID 551370Notes

Reaction equation

HRID 551370 reaction equation
[O:1]=[C:2]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:3](O)=[O:4].C(Cl)(=O)C([Cl:14])=O.CN(C=O)C>C(Cl)Cl>[O:1]=[C:2]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:3]([Cl:14])=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 776942-Thiopheneglyoxylic acid

Product 1

HCID 117451372-Chloro-1-(2-thienyl)-2-oxo-1-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of oxo-thiophen-2-yl-acetic acid (8 g, 51.2 mmol), suspended in DCM (80 ml) and cooled to 5° C., is added oxalylchloride (5.3 ml, 61.5 mmol), followed by DMF (0.1 ml). Stirring is continued for 1 hour at 5° C. and 18 hours at room temperature. The reaction mixture is evaporated to dryness, toluene is then added and the mixture is evaporated once more to give the title compound as a dark oil.

Workup

  1. customThe reaction mixture is evaporated to dryness, toluene
  2. additionis then added
  3. customthe mixture is evaporated once more

Sources & evidence

ORD record
ord-468fefaea73143b48f21294ed01b7c3b
Source dataset
uspto-grants-2011_05
Patent number
US07947730B2

Reaction notes

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