Sodium methanethiolate → HCID 86229871, compound

HRID 1713275Notes

Reaction equation

HRID 1713275 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:16][S-:17].[Na+]>CN(C)C=O>[CH3:16][S:17][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 167685272-Fluoro-4-phenylbenzaldehyde

Product 1

HCID 86229871HCID 86229871, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-fluoro-4-phenylbenzaldehyde (0.400 g) in N,N-dimethylformamide (4 mL) was added sodium methane-thiolate (0.210 g), and the resulting mixture was stirred at 50° C. for 2.5 hours. The reaction mixture was cooled to room temperature and then partitioned between diethyl ether (30 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.387 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between diethyl ether (30 mL) and water (10 mL)
  3. washThe organic layer was washed successively with water (10 mL×2) and brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e62b7babc314df19096a3c6d95b804c
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

Loading…