Phosphorus sulfide (P2S5) → 5-(5-Bromo-2-fluoro-phenyl)-5-difluoromethyl-2-methyl-morpholine-3-thione

HRID 221741Notes

Reaction equation

HRID 221741 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2([CH:16]([F:18])[F:17])[NH:13][C:12](=O)[CH:11]([CH3:15])[O:10][CH2:9]2)[CH:7]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2([CH:16]([F:18])[F:17])[NH:13][C:12](=[S:21])[CH:11]([CH3:15])[O:10][CH2:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 666659295-(5-Bromo-2-fluoro-phenyl)-5-difluoromethyl-2-methyl-morpholin-3-one

Product 1

HCID 866502665-(5-Bromo-2-fluoro-phenyl)-5-difluoromethyl-2-methyl-morpholine-3-thioneYield 102%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-2-methyl-morpholin-3-one (659 mg, 1.949 mmol) in 6.6 mL pyridine was added phosphorus pentasulfide (433 mg, 1.949 mmol) and the mixture was heated to 80° C. for 120 minutes. The reaction mixture was cooled to room temperature and partitioned between 0.1 N NaOH and EtOAc. The layers were separated, washed with brine and EtOAc. The combined organic layers were dried over MgSO4.H2O and evaporated to give 704 mg of the title compound as a diastereomeric mixture.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between 0.1 N NaOH and EtOAc
  3. customThe layers were separated
  4. washwashed with brine and EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4.H2O
  6. customevaporated

Sources & evidence

ORD record
ord-0e1e84b7138749fb993ef43917a8e0e9
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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