Potassium Fluoride → HCID 13282760, compound

HRID 746139Notes

Reaction equation

HRID 746139 reaction equation
Cl[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[F-:16].[K+].[K]>O1CCOCCOCCOCCOCCOCC1>[F:16][C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1

Participants

5

Reactant 3

HCID 522689Potassium Fluoride2×HCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylateHCID 5462222Potassium

Product 1

HCID 13282760HCID 13282760, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst2×

Procedure

A mixture of 26 g (0.1 mole) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate, 37 g (0.55 mole) of potassium fluoride, and 0.11 g of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-CROWN-6, Aldrich Chemical Company) was held at reflux for 23 hours. Since an analysis showed the reaction to be incomplete, another 45 g (0.77 mole) of potassium fluoride was added and the reaction mixture held at reflux for 64 hours. To said mixture, 0.15 g of 18-CROWN-6 and an additional 27 g (0.40 mole) of potassium was added and held at reflux for 22 hours. Due to poor cooling overnight some of the solvent had evaporated. The reaction mixture was cooled and 300 ml of acetonitrile added. The acetonitrile was filtered and concentrated. The residue was Kugelrohr distilled to give 13.7 g of a material which was separated by spinning band column at 15 mm Hg to give 4.2 g of the desired product, nD24 =1.4348.

Workup

  1. temperatureat reflux for 23 hours
  2. customthe reaction
  3. temperatureat reflux for 64 hours
  4. temperatureat reflux for 22 hours
  5. temperatureDue to poor cooling overnight some of the solvent
  6. customhad evaporated
  7. temperatureThe reaction mixture was cooled
  8. addition300 ml of acetonitrile added
  9. filtrationThe acetonitrile was filtered
  10. concentrationconcentrated
  11. distillationdistilled

Sources & evidence

ORD record
ord-baa20ca086374f44942c4f52b5a9747e
Source dataset
uspto-grants-1986_07
Patent number
US04602937

Reaction notes

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