Methyl Thioglycolate → HCID 20271316, compound

HRID 1758082Notes

Reaction equation

HRID 1758082 reaction equation
C[O-].[Na+].Cl.[N:5]1[CH:10]=[CH:9][C:8]([CH2:11]Cl)=[CH:7][CH:6]=1.[SH:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]>CO>[N:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 20271316HCID 20271316, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Sodium methoxide (2.16 g., 40 mmoles) is dissolved in 24 ml. of methanol, stirring under nitrogen, and the solution cooled in an ice bath. 4-Picolyl chloride hydrochloride (3.38 g., 20 mmoles), finely divided and suspended in approximately 20 ml. of methanol, is added dropwise over approximately 15 minutes. A solution of methyl 2-mercaptoacetate (2.12 g., 20 mmoles) in 4 ml. of methanol is then added over approximately 5 minutes. The reaction mixture is warmed slowly and left to stir under nitrogen for 14 hours at room temperature. The reaction is filtered with diatomaceous earth. Solids are repulped with an additional 75 ml. of methanol. The methanol filtrates are combined and concentrated to yield title product.

Workup

  1. temperaturethe solution cooled in an ice bath
  2. temperatureThe reaction mixture is warmed slowly
  3. waitleft
  4. filtrationThe reaction is filtered with diatomaceous earth
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b7c549db59854184aa2e8a62224ce2e0
Source dataset
uspto-grants-1983_02
Patent number
US04371696

Reaction notes

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