Lawesson's reagent → HCID 15039191, compound

HRID 2211181Notes

Reaction equation

HRID 2211181 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]([F:42])([F:41])[C:25]1[CH:26]=[C:27]([NH:31][C:32]2[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=2[C:34]([NH2:36])=O)[CH:28]=[CH:29][CH:30]=1>O1CCCC1>[F:23][C:24]([F:42])([F:41])[C:25]1[CH:26]=[C:27]([NH:31][C:32]2[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=2[C:34](=[S:10])[NH2:36])[CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 7864692-[3-(trifluoromethyl)anilino]benzamide

Product 1

HCID 15039191HCID 15039191, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lawesson's Reagent (4.55 g, 11.26 mmoles) is added to a colorless solution of 2-[(3-trifluoromethylphenyl)amino]-benzamide (5.22 g, 18.64 mmoles) in 100 ml of tetrahydrofuran at room temperature. The resulting mixture is stirred under nitrogen for one hour, and then heated at reflux for 2.5 hours. The solution is concentrated in vacuo, and purified by flash chromatography with a gradient of 5:1 to 3:1 hexane/ethyl acetate as eluant, to provide 3.01 g (55%) of a bright yellow solid 2-[(3-trifluoromethylphenyl)amino]-benzene thioamide, mp 106°-108° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. concentrationThe solution is concentrated in vacuo
  4. custompurified by flash chromatography with a gradient of 5:1 to 3:1 hexane/ethyl acetate as eluant

Sources & evidence

ORD record
ord-05e75794bebb4797bb765a1e0aef109e
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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