Lawesson's reagent → HCID 86721266, compound

HRID 1750425Notes

Reaction equation

HRID 1750425 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][N:7]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)(=O)[NH2:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1COCC1>[C:1]([C:4]1[CH:5]=[N:6][N:7]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)(=[S:32])[NH2:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86721267HCID 86721267, compound

Product 1

HCID 86721266HCID 86721266, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the mixture (711 mg, 2.33 mmol) obtained in step 5 and Lawesson's reagent (754 mg, 1.86 mmol) in THF (10 mL) was stirred at 60° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was treated with ethyl acetate and diethyl ether to give a mixture (415 mg, 55%) of tert-butyl 4-carbamothioyl-5-(4-fluorophenyl)-1H-pyrazole-1-carboxylate and tert-butyl 4-carbamothioyl-3-(4-fluorophenyl)-1H-pyrazole-1-carboxylate as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was treated with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-f6bf3a0e312e40ea965e1e4bd8e27842
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

Loading…