Sodium methanethiolate → HCID 89656428, compound

HRID 633550Notes

Reaction equation

HRID 633550 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 52C (1.512 g, 4.00 mmol) and sodium thiomethoxide (0.280 g, 4.00 mmol) in dimethylformamide (8 mL) was stirred at room 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-a27f162a1d604caab5a709a2e8968ec3
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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