Lawesson's reagent → HCID 86640020, compound

HRID 1673058Notes

Reaction equation

HRID 1673058 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[C:12]([C:14]([NH2:16])=O)[N:11]=[CH:10]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1C=CC=CC=1>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[C:12]([C:14](=[S:28])[NH2:16])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22285543HCID 22285543, compound

Product 1

HCID 86640020HCID 86640020, compoundYield 184.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(3′-methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl-1H-imidazole-4-carboxamide (243 mg, 0.5 mmol), Lawesson's reagent (243 mg, 0.6 mmol), and dry benzene (15 mL) was stirred at reflux for 2 h. The solvent was removed in vacuo, and the crude product was purified by flash chromatography (SiO2, 90% EtOAc/hexanes) to give 1-(3′-methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl-1H-imidazole-4-carbothioamide as a yellow solid (250 mg, 100%). MS (ESI) 502 [M+H]+.

Workup

  1. temperatureat reflux for 2 h
  2. customThe solvent was removed in vacuo
  3. customthe crude product was purified by flash chromatography (SiO2, 90% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3a911df87ba14be39463a46c5a292042
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

Loading…