Lawesson's reagent → HCID 19754667, compound

HRID 1588788Notes

Reaction equation

HRID 1588788 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([C:16]2[C:17]([CH:22]([F:24])[F:23])=[N:18][N:19]([CH3:21])[CH:20]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([C:16]2[C:17]([CH:22]([F:24])[F:23])=[N:18][N:19]([CH3:21])[CH:20]=2)=[S:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19754706HCID 19754706, compound

Product 1

HCID 19754667HCID 19754667, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(2-cyclohexylphenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (2.0 g) and Lawesson's reagent (2.4 g) were refluxed in toluene (100 mL) for 1 h. Contents were stirred overnight at RT and filtered. The filtrate was concentrated in vacuo leaving a yellow solid which was chromatographed on silica gel eluting with 35% EtOAc/hexanes to give a yellow solid. The solid was recrystallized from EtOAc to give the desired compound as a yellow solid (1.1 g).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customleaving a yellow solid which
  4. customwas chromatographed on silica gel eluting with 35% EtOAc/hexanes
  5. customto give a yellow solid
  6. customThe solid was recrystallized from EtOAc

Sources & evidence

ORD record
ord-c22b1844b1844927a8c0370043448661
Source dataset
uspto-grants-1993_06
Patent number
US05223526

Reaction notes

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