Sodium methanethiolate → HCID 89656428, compound

HRID 930920Notes

Reaction equation

HRID 930920 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[CH:5]=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18].[CH3:19][S-:20].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])[CH2:8][S:20][CH3:19]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 89656327HCID 89656327, compound

Product 1

HCID 89656428HCID 89656428, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 287c (1.512 g, 4.00 mmol) and sodium thiomethoxide (0.280 g, 4.00 mmol) in dimethylformamide (8 mL) was stirred at ambient temperature for 6 hours. The reaction mixture was partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride twice, dried with anhydrous sodium sulfate, filtered, and concentrated to provide the title compound (1.38 g, 100%).

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and water
  2. washThe organic layer was washed with saturated aqueous sodium chloride twice
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a548a78a2094b56afa27965de547ab9
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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