Lawesson's reagent → HCID 18546409, compound

HRID 2211172Notes

Reaction equation

HRID 2211172 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.[Cl:23][C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[C:26]([Cl:31])[C:25]=1[NH:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1C(N)=O>O1CCCC1>[Cl:23][C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[C:26]([Cl:31])[C:25]=1[NH:32][C:33]1[CH:34]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 14951346HCID 14951346, compound

Product 1

HCID 18546409HCID 18546409, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lawesson's Reagent (2.67 g, 6.60 mmol) is added to a colorless solution of 2-[(2,6-dichloro-3-methylphenyl)amino]-benzamide (2.83 g, 9.60 mmol) in 50 ml of tetrahydrofuran at room temperature. The resulting mixture is stirred under nitrogen for three days. The clear yellow solution is then heated at reflux for two hours. The solution is concentrated in vacuo and chromatographed, eluting with hexane:ethyl acetate (gradient of 6:1 to 3:1), providing 1.71 g (57%) of a pale yellow solid.

Workup

  1. temperatureThe clear yellow solution is then heated
  2. temperatureat reflux for two hours
  3. concentrationThe solution is concentrated in vacuo
  4. customchromatographed
  5. washeluting with hexane

Sources & evidence

ORD record
ord-56f1e5742e124e268dbd3fd105187b20
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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