Lawesson's reagent → HCID 86675148, compound

HRID 1503684Notes

Reaction equation

HRID 1503684 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 RT 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-6993f223ca2b4b8389f1969edc48513c
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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