tert-Butyl chloroacetate → tert-Butyl [(ethoxycarbonothioyl)sulfanyl]acetate

HRID 2409382Notes

Reaction equation

HRID 2409382 reaction equation
[CH2:1]([O:3][C:4]([S-:6])=[S:5])[CH3:2].[K+].Cl[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>CC(C)=O>[C:4](=[S:6])([O:3][CH2:1][CH3:2])[S:5][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 66052tert-Butyl chloroacetateHCID 2735045Potassium ethylxanthate

Product 1

HCID 10857462tert-Butyl [(ethoxycarbonothioyl)sulfanyl]acetateYield 102%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium ethylxanthate (58.0 g, 364 mmol) was suspended in 200 mL of dry acetone at room temperature. tert-Butyl chloroacetate (50 g, 332 mmol) was added dropwise with stirring. After 18 hrs potassium chloride was removed by fitration, and the solvent was evaporated. The residue was taken up into ether, washed with 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and evaporated to leave 80 g of O-ethyl S-(tert-butoxycarbonyl)methyl dithiocarbonate as a thick oil. This oil was stirred with ethanolamine (323 mmol) for 2 hrs at room temperature. The reaction mixture was taken up into ethyl acetate, washed with 1.2N HCl, water, and brine, dried over MgSO4, filtered, and evaporated. The residue was vacuum dis-tilled to give 30 g of mercapto-acetic acid tert-butyl ester as a clear oil.

Workup

  1. customAfter 18 hrs potassium chloride was removed by fitration
  2. customthe solvent was evaporated
  3. washwashed with 5% NaHCO3, water, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6d1d202542f94b8abaa982854d350aba
Source dataset
uspto-grants-2014_08
Patent number
US08815873B2

Reaction notes

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