Methanethiol → 4-[3-Fluoro-5-(methylthio)phenyl]tetrahydro-2H-pyran-4-carbonitrile

HRID 1108099Notes

Reaction equation

HRID 1108099 reaction equation
[CH3:1][SH:2].[H-].[Na+].[C:5]([C:7]1([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15](F)[CH:14]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)#[N:6].O>CN(C=O)C>[C:5]([C:7]1([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([S:2][CH3:1])[CH:14]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)#[N:6]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 24758Sodium hydrideHCID 111487844-(3,5-difluorophenyl)tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 112421714-[3-Fluoro-5-(methylthio)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methanethiol was bubbled into a stirred suspension of sodium hydride (65% w/w dispersion in mineral oil, 273 mg, 7.4 mmol) in DMF (10 ml) until a clear solution was obtained. 4-Cyano-4-(3,5-difluorophenyl)-3,4,5,6-tetrahydro-2H-pyran (1.65 g, 7.4 mmol) was added and the resulting mixture was heated at 100° C. for 22 h, cooled and poured into water (100 ml). The mixture was extracted with Et2O (100 ml) and extract washed with water (100 ml), brine (100 ml) and dried (MgSO4). Removal of solvent gave 1.87 g (quant.) of the titled compound as a tan oil.

Workup

  1. customwas obtained
  2. temperaturecooled
  3. extractionThe mixture was extracted with Et2O (100 ml)
  4. extractionextract
  5. washwashed with water (100 ml), brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-c8b970e9e7344dc9b0e6c7bb25d20430
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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