Methyl Thioglycolate → HCID 17609605, compound

HRID 493962Notes

Reaction equation

HRID 493962 reaction equation
[H-].[Na+].Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1.[C:13]([O:17][CH3:18])(=[O:16])[CH2:14][SH:15]>O1CCCC1>[CH3:18][O:17][C:13]([CH2:14][S:15][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:16]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 17609605HCID 17609605, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

First, 0.8 g of sodium hydride was added to a mixture of 3.17 g of 2-chloro-3-nitropyridine, 2.12 g of methyl thioglycolate, and 20 ml of tetrahydrofuran at 0° C. After stirring at room temperature for 2 hours, the reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was washed with diisopropyl ether and hexane to give 3.1 g of 2-(methoxycarbonyl)methylthio-3 -nitropyridine.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. washThe residue was washed with diisopropyl ether and hexane

Sources & evidence

ORD record
ord-f5d20b07f2fd4b06914d5ae0ab897ca6
Source dataset
uspto-grants-2009_05
Patent number
US07538072B2

Reaction notes

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