Methanol → HCID 20426456, compound

HRID 615595Notes

Reaction equation

HRID 615595 reaction equation
C[O-].[Na+].CO.[SH:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].[CH:12]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)=[CH2:13]>C(O)C>[N:17]1[CH:18]=[CH:19][C:14]([CH2:12][CH2:13][S:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 75024-VinylpyridineHCID 16907Methyl ThioglycolateHCID 10942334Sodium Methoxide

Product 1

HCID 20426456HCID 20426456, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, sodium methoxide (1.62 g., 0.03 mole) is dissolved in 36 ml. of stirring methanol and the solution cooled in an ice bath. Methyl 2-mercaptoacetate (3.18 g., 0.03 mole) in 6 ml. of methanol is added over approximately 5 minutes. Finally, 4-vinylpyridine (3.22 g., 0.03 mole) in approximately 20 ml. of absolute ethanol is added over 15 minutes. The reaction mixture is allowed to warm to room temperature and stirred for 23 hours. The reaction mixture is concentrated to dryness in vacuo. The residue is added slowly to a stirred mixture of water and chloroform. The chloroform phase is separated and the aqueous phase further extracted with chloroform. The combined chloroform phases are extracted with saturated sodium chloride, dried over anhydrous sodium sulfate, and stripped to yield title product.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness in vacuo
  2. additionThe residue is added slowly to a stirred mixture of water and chloroform
  3. customThe chloroform phase is separated
  4. extractionthe aqueous phase further extracted with chloroform
  5. extractionThe combined chloroform phases are extracted with saturated sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-673bd1eb25994f678496a3a2cd51bbfa
Source dataset
uspto-grants-1985_02
Patent number
US04500535

Reaction notes

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