Sodium methanethiolate → HCID 67468084, compound

HRID 1406295Notes

Reaction equation

HRID 1406295 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7]Cl)=[N:4][CH:3]=1.[CH3:9][S-:10].[Na+]>CN(C=O)C>[Br:1][C:2]1[S:6][C:5]([CH2:7][S:10][CH3:9])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 662211065-Bromo-2-(chloromethyl)-1,3-thiazole

Product 1

HCID 67468084HCID 67468084, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-(chloromethyl)thiazole (177 mg, 0.833 mmol) was stirred in DMF (10 mL) under nitrogen at room temperature and sodium thiomethoxide (117 mg, 1.67 mmol) was added. The mixture was stirred overnight and concentrated. The residue was slurried in ethyl acetate (30 ml), washed with water, dried over sodium sulfate, and concentrated to give a brown oil which was purified by ISCO CombiFlash® chromatography with Heptane:DCM (100:0 to 0:100 over 10 column volume and held for a further 10 CV to give the product as a brown oil (53 mg 28%).

Workup

  1. concentrationconcentrated
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a brown oil which
  6. customwas purified by ISCO CombiFlash® chromatography with Heptane:DCM (100:0 to 0:100 over 10 column volume

Sources & evidence

ORD record
ord-36d66fbef9e641388b5c1fbb0022a185
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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