Sodium Hydroxide → HCID 178526006, compound

HRID 1380692Notes

Reaction equation

HRID 1380692 reaction equation
[C:1]([CH2:6][N:7]1[C:11]([SH:12])=[N:10][N:9]=[N:8]1)([C:3]([OH:5])=[O:4])=[O:2].[OH-].[Na+]>C(O)C.[Zn]>[C:3]([CH:1]([OH:2])[CH2:6][N:7]1[C:11]([SH:12])=[N:10][N:9]=[N:8]1)([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178526005HCID 178526005, compound

Product 1

HCID 178526006HCID 178526006, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

1-Oxalomethyl-1H-tetrazole-5-thiol (0.94 g) was dissolved in aqueous 60% ethanol (15 ml) containing sodium hydroxide (1.4 g) and to this solution was added portionwise zinc powder (0.98 g). The mixture was stirred at room temperature for 3.5 hours. After removal of zinc powder by filtration, ethanol was removed under reduced pressure and the remained aqueous solution was adjusted to pH 2.0 with 10% hydrochloric acid. Extraction with ethyl acetate, drying over magnesium sulfate and evaporation gave an oil which was triturated with a mixture of diisopropyl ether and n-hexane (1:1). The crystals were filtered and washed with a mixture of diisopropyl ether and n-hexane (1:1) to give 1-(2-carboxy-2-hydroxyethyl)-1H-tetrazole-5-thiol (0.40 g), mp 143° to 146° C.,

Workup

  1. customAfter removal of zinc powder
  2. filtrationby filtration, ethanol
  3. customwas removed under reduced pressure
  4. extractionExtraction with ethyl acetate
  5. dry with materialdrying over magnesium sulfate and evaporation
  6. customgave an oil which
  7. customwas triturated with a mixture of diisopropyl ether and n-hexane (1:1)
  8. filtrationThe crystals were filtered
  9. washwashed with a mixture of diisopropyl ether and n-hexane (1:1)

Sources & evidence

ORD record
ord-3fc1e50a9401407d98758af80ea5cd7c
Source dataset
uspto-grants-1986_04
Patent number
US04582908

Reaction notes

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