Lawesson's reagent → HCID 86721228, compound

HRID 1750388Notes

Reaction equation

HRID 1750388 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[C:14]([NH2:16])=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[C:14](=[S:26])[NH2:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86721229HCID 86721229, compound

Product 1

HCID 86721228HCID 86721228, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound (446 mg, 2.04 mmol) obtained in step 3 and Lawesson's reagent (658 mg, 1.63 mmol) in THF (8.5 mL) was heated at 60° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (solvent gradient; 20→50% ethyl acetate/hexane) to give a mixture (3:2 (mol/mol), 319 mg, 67%) of 5-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbothioamide and 3-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbothioamide as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by NH-silica gel column chromatography (solvent gradient; 20→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6303dafc1f234255a2e2a4d8371d77e2
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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