Lawesson's reagent → HCID 86674816, compound

HRID 1910844Notes

Reaction equation

HRID 1910844 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([NH2:15])=O)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[S:27])[NH2:15])[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67343043HCID 67343043, compound

Product 1

HCID 86674816HCID 86674816, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 22987606Toluene trichloromethaneSolvent

Procedure

According to Scheme 1 Step 4: A solution of 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxamide (109 mmol, 25.1 g) and Lawesson's reagent (109 mmol, 43.9 g) in CHCl3/toluene (1:1, 136 mL) was stirred at 85° C. for 12 hours. The reaction mixture was evaporated and the residue was recrystallized in EtOAc/pentane to yield 13.8 g of 1-(4-methoxybenzyl)-1H-pyrazole-4-carbothioamide. The mother liquors were evaporated and the crude residue was purified by flash chromatography over silica gel using DCM/EtOAc (100:0 to 70:30) to yield 1-(4-methoxybenzyl)-1H-pyrazole-4-carbothioamide (94.6 mmol, 23.4 g, 87%) as a beige solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was recrystallized in EtOAc/pentane

Sources & evidence

ORD record
ord-19870d9455c54147b88fb79e44b11642
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

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