Lawesson's reagent → 4-(2,3-Difluoro-phenylthiocarbamoyl)-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2249518Notes

Reaction equation

HRID 2249518 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:7]=[C:8]([C:10](=O)[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[CH:9]=1)=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:7]=[C:8]([C:10](=[S:34])[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58685821HCID 58685821, compound

Product 1

HCID 586858224-(2,3-Difluoro-phenylthiocarbamoyl)-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl esterYield 143.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(2,3-difluoro-phenylcarbamoyl)-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl ester (410 mg, 1.14 mmol) in dry toluene (10 mL) was added Lawesson's reagent (320 mg, 0.79 mmol). The suspension was heated at reflux for 2 hours. The solvent was removed by evaporation and the residue was purified by flash column eluting with 30% of EtOAc/hexanes to afford the title compound as a yellow solid (425 mg, 99%). MS (ES+): m/e=375.1 (M+H); LC/Method A/3.61 min.

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed by evaporation
  4. customthe residue was purified by flash column
  5. washeluting with 30% of EtOAc/hexanes

Sources & evidence

ORD record
ord-7e322bb186db4e18904981808e3af4d7
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

Loading…