Methyl Thioglycolate → HCID 20271316, compound

HRID 615585Notes

Reaction equation

HRID 615585 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-c14937901f9243d7909d46b5c9080600
Source dataset
uspto-grants-1985_02
Patent number
US04500535

Reaction notes

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