Lawesson's reagent → 5-(5-Bromo-2-fluorophenyl)-5-methylmorpholine-3-thione

HRID 925445Notes

Reaction equation

HRID 925445 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2([CH3:15])[NH:13][C:12](=O)[CH2:11][O:10][CH2:9]2)[CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2([CH3:15])[NH:13][C:12](=[S:26])[CH2:11][O:10][CH2:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 581552625-(5-Bromo-2-fluorophenyl)-5-methylmorpholin-3-one

Product 1

HCID 888502225-(5-Bromo-2-fluorophenyl)-5-methylmorpholine-3-thione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholin-3-one (CAS registry 1266784-13-7) (26.0 g, 82 mmol) in THF (520 ml) was added Lawesson's reagent (33.91 g, 82 mmol) and the reaction was heated for 2 h at reflux, then stirred for 14 h at rt. The solvent was evaporated and the title compound was prepurified by FC (toluene). Remaining impurities were removed by washing the toluene fractions with sat. aq. NaHCO3 soln. and water, the combined organic layers were dried over Na2SO4 and concentrated. Crude product was washed with MTBE and used in the next step without further purification.

Workup

  1. temperaturethe reaction was heated for 2 h
  2. temperatureat reflux
  3. customThe solvent was evaporated
  4. customRemaining impurities were removed
  5. washby washing the toluene fractions with sat. aq. NaHCO3 soln
  6. dry with materialand water, the combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. washCrude product was washed with MTBE
  9. customused in the next step without further purification

Sources & evidence

ORD record
ord-89c5feb37f544e2aa7188bca5c9d71bb
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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