Sodium ethanethiolate → HCID 89656356, compound

HRID 633551Notes

Reaction equation

HRID 633551 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].[CH2:19]([S-:21])[CH3:20].[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:21][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 89656327HCID 89656327, compound

Product 1

HCID 89656356HCID 89656356, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 52C (1.10 g, 2.91 mmol) and sodium ethanethiolate (0.245 g, 2.91 mmol) in dimethylformamide (10 mL) was stirred at ambient temperature for 4 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 (1.04 g, 99%).

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-6a0609fd58c24e0e8ea262c531e6c931
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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