2-Thiophenecarbonyl chloride → HCID 15917157, compound

HRID 2229822Notes

Reaction equation

HRID 2229822 reaction equation
[S-:1][C:2]#[N:3].[K+].[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10](Cl)=[O:11]>CC(C)=O>[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10]([N:3]=[C:2]=[S:1])=[O:11]

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 516872Potassium thiocyanate

Product 1

HCID 15917157HCID 15917157, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a freshly prepared solution of potassium thiocyanate (2.14 g, 22 mmol) in dry acetone (80 ml ), thiophene-2-carbonyl chloride (2.93 g, 20 mmol) was added dropwise at room temperature; the reaction mixture was then heated under a reflux for 15 min to give thiophene-2-carbonyl isothiocyanate in situ as a yellow suspension. The heating was stopped and 2-imidazolidinethione (2.04 g, 20 mmol) was added. The mixture was then heated under reflux for an additional 4 hours before being allowed to cool followed by stirring at room temperature overnight (15 hours). 50 ml of water was added and the mixture was further stirred at room temperature for a few minutes. The resulting precipitate was collected by filtration and washed with water, water/methanol (1:1) and methanol to give the compound ARE111 (2.865 g, yield=53%)

Workup

  1. temperaturethe reaction mixture was then heated under
  2. temperaturea reflux for 15 min

Sources & evidence

ORD record
ord-70422e9dbbe64ea3ba33ee489bf5f9ae
Source dataset
uspto-grants-2002_07
Patent number
US06420563B1

Reaction notes

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