Water → HCID 54136215, compound

HRID 1978815Notes

Reaction equation

HRID 1978815 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Cl.[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:1]([O:4][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][N:7]=1)(=[S:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 23670855Potassium ethanethioate

Product 1

HCID 54136215HCID 54136215, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium thioacetate (8.4 g, 73 mmol), 2-picolyl chloride hydrochloride 1 (6.0 g, 37 mmol) and potassium carbonate (5.0 g, 37 mmol) were stirred in DMF (35 mL) at room temperature (20-22°) for 18 h. The reaction mixture was poured into water (200 mL). The resultant mixture was extracted with Et2O (2×50 mL). The combined organic phases were washed with water and brine, dried (MgSO4), filtered and concentrated to give 2-picolyl thioacetate as a pale brown liquid (5.65 g). The product was used without purification.

Workup

  1. extractionThe resultant mixture was extracted with Et2O (2×50 mL)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e0dae93fa5c84191be5e7b59216d9516
Source dataset
uspto-grants-2001_05
Patent number
US06239125B1

Reaction notes

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