Lawesson's reagent → HCID 65694378, compound

HRID 1894718Notes

Reaction equation

HRID 1894718 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7]([C:9]1[NH:13][N:12]=[CH:11][CH:10]=1)=O)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1COCC1>[Cl:1][CH2:2][C:3]1[S:23][C:7]([C:9]2[NH:13][N:12]=[CH:11][CH:10]=2)=[N:6][N:5]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66646977HCID 66646977, compound

Product 1

HCID 65694378HCID 65694378, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N′-(2-chloroacetyl)-1H-pyrazole-5-carbohydrazide (110 mg, 0.54 mmol) and Lawesson's reagent (220 mg, 0.54 mmol) were suspended in THF 5.5 mL and then heated to reflux for 3 hr. The reaction mixture was concentrated and chromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes to give the title compound as white solid (60.5 mg).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated
  4. customchromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes

Sources & evidence

ORD record
ord-291ed9f58c2a4ebca4312ff43295c443
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

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