Lawesson's reagent → HCID 14424279, compound

HRID 414224Notes

Reaction equation

HRID 414224 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][C:24]1[S:28][C:27]([C:29](=O)[CH2:30][NH:31][C:32](=O)[C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:23][C:24]1[S:28][C:27]([C:29]2[S:10][C:32]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=3)=[N:31][CH:30]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 14424278HCID 14424278, compound

Product 1

HCID 14424279HCID 14424279, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of Lawesson's Reagent (2.3 g, 0.0057 mole) in approximately 40 ml of toluene was added a mixture of N-[2-(5-methylthienyl)-2-oxoethyl]-4-trifluoromethylbenzamide (3.0 g, 0.011 mole) in toluene (35 ml). After complete addition the reaction mixture was heated at reflux for approximately four hours, then was allowed to cool to room temperature and stirred for two days. The solvent was removed from the reaction mixture by evaporation under reduced pressure, leaving an oil. The oil was dissolved in a small amount of methylene chloride and purified by column chromatography on silica gel, eluting with methylene chloride, yielding 1.0 g of 5-(5-methylthien-2-yl)-2-(4-trifluoromethylphenyl)thiazole as a solid, m.p. 150°-152° C.

Workup

  1. additionwas added
  2. additionAfter complete addition the reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for approximately four hours
  5. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure
  6. customleaving an oil
  7. custompurified by column chromatography on silica gel
  8. washeluting with methylene chloride

Sources & evidence

ORD record
ord-ef927fe9fdb84ec9ba860d24af4838be
Source dataset
uspto-grants-1988_12
Patent number
US04791124

Reaction notes

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