Lawesson's reagent → HCID 23023848, compound

HRID 851872Notes

Reaction equation

HRID 851872 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=O)#[N:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=[S:34])#[N:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 23023849HCID 23023849, compound

Product 1

HCID 23023848HCID 23023848, compoundYield 132.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 3-cyano-4-isobutyloxy-N-(3-methoxyphenyl)benzamide (972 mg, 3.0 mmol) and Lawesson's reagent (808 mg, 2.0 mmol) in toluene (5 mL) was heated under reflux for 3.5 hours. After addition of toluene (approx. 20 mL), the heated solution was allowed overnight to lapse at room temperature. The precipitated crystalline product was collected by filtration, to give 900 mg (yield 88%) of the desired compound in the form of a yellow crystalline product.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. customto lapse at room temperature
  3. filtrationThe precipitated crystalline product was collected by filtration

Sources & evidence

ORD record
ord-89215e0211a246fe95720268fb32c7d9
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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