Lawesson's reagent → HCID 86675148, compound

HRID 1502684Notes

Reaction equation

HRID 1502684 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[CH:19]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)[C:20]([F:23])([F:22])[F:21])=[CH:13][C:12]=2[CH3:32])=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[S:43])[C:11]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[CH:19]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)[C:20]([F:23])([F:22])[F:21])=[CH:13][C:12]=2[CH3:32])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86675149HCID 86675149, compound

Product 1

HCID 86675148HCID 86675148, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the stirred solution of (E)-N-((6-chloropyridin-3-yl)methyl)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzamide (0.06 g, 0.117 mmol) in toluene (3 mL) was added Lawesson's reagent (0.14 g, 0.351 mmol) and the reaction was irradiated at 100° C. for 1 h, then cooled to ambient temperature and concentrated under reduced pressure to provide crude compound. The crude product was purified by preparative HPLC to afford the product as yellow color solid (0.03 g, 49%).

Workup

  1. customthe reaction was irradiated at 100° C. for 1 h
  2. concentrationconcentrated under reduced pressure
  3. customto provide crude compound
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-b5b002ed45134003ae757b215e42d97f
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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