Dimethylformamide → HCID 68643648, compound

HRID 1987483Notes

Reaction equation

HRID 1987483 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]C)=[O:10])=[CH:5][CH:4]=1.CN(C=O)C>CCCCCC.C(OCC)(=O)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[SH:17])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 24722794(4-Methoxyphenyl)[2-(methylsulfanyl)phenyl]methanone

Product 1

HCID 68643648HCID 68643648, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a nitrogen flushed mixture of 1.415 g (4-methoxyphenyl)(2-(methylthio)phenyl)methanone (C) (5.48 mmol) and 3 g sodium thiolate (26.6 mmol) was added 40 ml anhydrous DMF. The mixture was refluxed under nitrogen. After the mixture turned to black, the reaction was refluxed for two more hours cooled to RT and quenched with water. The mixture was washed ethyl acetate (2×100 ml). The combined organic was brined, dried over magnesium sulfate, filtered and concentrated. Flash column (hexane:ethyl acetate 80:20) yield 0.954 g product (4.0 mmol, 73% yield).

Workup

  1. customTo a nitrogen flushed
  2. temperatureThe mixture was refluxed under nitrogen
  3. temperaturewas refluxed for two more hours
  4. customquenched with water
  5. washThe mixture was washed ethyl acetate (2×100 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-345ce9c613fa4af481a2b33208276241
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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