Lawesson's reagent → HCID 14424293, compound

HRID 1165125Notes

Reaction equation

HRID 1165125 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:31]2)=CC=1>C1(C)C=CC=CC=1>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([C:9]2[S:31][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][N:8]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 14819305HCID 14819305, compound2×

Product 1

HCID 14424293HCID 14424293, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a dry nitrogen atmosphere N-[2-(thien-2-yl)-2-oxoethyl]-4-trifluoromethylbenzamide (5.6 g of the solid from Step D) was added to a stirred suspension of [2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) (3.6 g, 0.0090 mole) in 150 ml of toluene. The resultant mixture was heated at reflux for four hours, then was allowed to cool to room temperature, and was stirred for approximately 18 hours. The mixture was heated at reflux for three hours and then was cooled. The solvent was removed from the mixture by evaporation under reduced pressure, leaving a residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride:n-hexane (3:1) to yield 2.84 g of 2-(4-trifluoromethylphenyl)-5-thien-2-ylthiazole, as a solid, mp 153.5°-155° C.

Workup

  1. temperatureat reflux for four hours
  2. temperatureThe mixture was heated
  3. temperatureat reflux for three hours
  4. temperaturewas cooled
  5. customThe solvent was removed from the mixture by evaporation under reduced pressure
  6. customleaving a residue
  7. customThis residue was purified by column chromatography on silica gel
  8. washeluting with methylene chloride:n-hexane (3:1)

Sources & evidence

ORD record
ord-a2cdcb961f674a5aa1f95aefa03edc97
Source dataset
uspto-grants-1990_03
Patent number
US04908357

Reaction notes

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