Lawesson's reagent → HCID 24810042, compound

HRID 254819Notes

Reaction equation

HRID 254819 reaction equation
[CH:1]1([C:5]([NH:7][NH:8][C:9]([C:11]2[C:15]([CH3:16])=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:13]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[Cl:31])[N:12]=2)=O)=O)[CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>O1CCOCC1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:13]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[Cl:31])[N:12]=[C:11]([C:9]3[S:41][C:5]([CH:1]4[CH2:4][CH2:3][CH2:2]4)=[N:7][N:8]=3)[C:15]=2[CH3:16])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 25150145HCID 25150145, compound

Product 1

HCID 24810042HCID 24810042, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

N-cyclobutanoyl-N′-[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl]-hydrazine (0.14 g, 0.29 mmol) was added to a microwave reactor containing Lawesson's reagent (0.18 g, 0.44 mmol) in 1,4-dioxane (3 mL). The capped reactor was placed into a microwave reactor and the mixture was heated at 180° C. for 15 min, and the process was repeated one more time. The reaction mixture was then purified by preparative HPLC to provide the title compound (60 mg, 0.16 mmol, 43%) as yellow solid.

Workup

  1. customThe capped reactor was placed into a microwave reactor
  2. customThe reaction mixture was then purified by preparative HPLC

Sources & evidence

ORD record
ord-53050e59fab74d9987659a63273b7375
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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