Lawesson's reagent → HCID 18324932, compound

HRID 1250912Notes

Reaction equation

HRID 1250912 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=O)[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[O:10][C:9]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=[S:38])[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[O:10][C:9]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 18324902HCID 18324902, compound

Product 1

HCID 18324932HCID 18324932, compoundYield 171%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)-4H-1-benzopyran-4-one(0.45 g, 1.14 mmol) from Example 1 and Lawesson's reagent(0.23 g, 0.57 mmol) in toluene(10 ml) was refluxed for 1 hour. The resulting mixture was concentrated and subjected to flash chromatography using a mixture of hexane:ethyl acetate:dichloroethane(1:1:1) as an eluant to yield the title compound as a deep green solid(0.4 g, 85%).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiona mixture of hexane:ethyl acetate:dichloroethane(1:1:1) as an eluant

Sources & evidence

ORD record
ord-b892abda5e564644b4678bfe727d2834
Source dataset
uspto-grants-2002_01
Patent number
US06340694B1

Reaction notes

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