Hydrogen Sulfide → HCID 20330468, compound

HRID 2057804Notes

Reaction equation

HRID 2057804 reaction equation
[Na].[CH3:2][C:3]1[C:8]([O:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:7]([CH2:15][O:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]([CH2:22]Cl)=[CH:5][N:4]=1.[SH2:24]>CN(C)C=O>[CH3:2][C:3]1[C:8]([O:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:7]([CH2:15][O:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]([CH2:22][SH:24])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 402Hydrogen Sulfide2×HCID 5360545SodiumHCID 203304722-Methyl-3-ethoxycarbonyloxy-4-ethoxycarbonyloxymethyl-5-chloromethylpyridine

Product 1

HCID 20330468HCID 20330468, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.4 moles sodium in absolute dimethylformamide is saturated by passing in hydrogen sulfide for 5 hours. There is then added in portions 0.05 moles of 2-methyl-3-ethoxycarbonyloxy-4-ethoxycarbonyloxymethyl-5-chloromethylpyridine and the mixture stirred overnight at room temperature with hydrogen sulfide slowly bubbling through the mixture. The reaction mixture is then concentrated in vacuo and taken up between ethyl acetate and water containing acetic acid. The ethyl acetate layer is removed, dried over sodium sulfate and concentrated to give 2-methyl-3-ethoxycarbonyloxy-4-ethoxycarbonyloxymethyl-5-mercaptomethylpyridine.

Workup

  1. customslowly bubbling through the mixture
  2. concentrationThe reaction mixture is then concentrated in vacuo
  3. additioncontaining acetic acid
  4. customThe ethyl acetate layer is removed
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4017d21fae304f62be9924c26db465a3
Source dataset
uspto-grants-1980_07
Patent number
US04212976

Reaction notes

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