Lawesson's reagent → 5-(5-Bromo-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepane-3-thione

HRID 2196333Notes

Reaction equation

HRID 2196333 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2([CH3:18])[C:14]([F:16])([F:15])[CH2:13][O:12][CH2:11][C:10](=O)[NH:9]2)[CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2([CH3:18])[C:14]([F:16])([F:15])[CH2:13][O:12][CH2:11][C:10](=[S:29])[NH:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 666660575-(5-Bromo-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepan-3-one

Product 1

HCID 866502735-(5-Bromo-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepane-3-thione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-bromo-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepan-3-one (2.0 g, 5.93 mmol) in THF (25 mL) was added Lawesson's reagent (2.87 g, 7.1 mmol) at rt and heated to reflux temperature for 16 h. Reaction mixture was concentrated under reduced pressure and directly purified by column chromatography on silica gel using 4% ethyl acetate in Hexane to furnish title compound as colorless gum. Yield=1.0 g (50%). LCMS: RtH8=1.75 [M+H]+=354.8, 355.7,

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 16 h
  3. customReaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customdirectly purified by column chromatography on silica gel using 4% ethyl acetate in Hexane

Sources & evidence

ORD record
ord-9c60e42e3902461ca607f32532778d0e
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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