Pyridine → HCID 18180289, compound

HRID 1358985Notes

Reaction equation

HRID 1358985 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]([NH2:19])(=[S:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>CC(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:19][C:11](=[S:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 683563Thiobenzamide

Product 1

HCID 18180289HCID 18180289, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 4-fluorobenzoylchloride (1.3 g, 8.5 mmol) in acetone (7.0 ml) was added a solution of thiobenzamide (1.16 g, 8.5 mmol) and pyridine (0.66 g, 8.5 mmol) in acetone (7.0 ml). The mixture was refluxed for 6 h. and cooled to room temperature. The reaction mixture was poured into water/ice and extracted with chloroform. Flash chromatography on silica gel afforded 0.5 g of the title compound as a red solid.

Workup

  1. temperatureThe mixture was refluxed for 6 h.
  2. extractionextracted with chloroform

Sources & evidence

ORD record
ord-a2135d4ca5174f218720783ac0257b21
Source dataset
uspto-grants-2003_07
Patent number
US06599910B1

Reaction notes

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