Lawesson's reagent → HCID 18694307, compound

HRID 1870882Notes

Reaction equation

HRID 1870882 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=O)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[S:33])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10990514HCID 10990514, compound

Product 1

HCID 18694307HCID 18694307, compoundYield 121.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

Methyl 2'-methyl-4'-(2-oxo-1-pyrrolidinyl)biphenyl-4-carboxylate (D4, 200 mg, 0.647 mmol) was dissolved in toluene (25 ml) and Lawesson's reagent (130 mg, 0.324 mmol) was added. The solution was heated at 75° C. under argon for 1.5 hrs, then concentrated in vacuo. The resultant pale yellow solid was filtered through a neutral alumina column eluting with ether to remove excess Lawesson's reagent, then purified by column chromatography on silica gel eluting with ether to afford the title compound as a yellow solid (128 mg, 61%).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationThe resultant pale yellow solid was filtered through a neutral alumina column
  3. washeluting with ether
  4. customto remove excess Lawesson's reagent
  5. custompurified by column chromatography on silica gel eluting with ether

Sources & evidence

ORD record
ord-f7aab15c122c4af19b778bea1455a6e7
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

Loading…