Hydrogen Sulfide → HCID 135819067, compound

HRID 1579057Notes

Reaction equation

HRID 1579057 reaction equation
C(O[C:5]1[CH:20]=[CH:19][C:8]([C:9]([C:11](=[N+]=[N-])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)=[CH:7][CH:6]=1)(=O)C.[NH4+:21].[NH4+:22].[S-]S[S-].[SH2:26].C([OH:29])C>>[OH:29][C:19]1[CH:20]=[CH:5][CH:6]=[CH:7][C:8]=1[C:9]1[S:26][N:22]=[N:21][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 4

HCID 402Hydrogen SulfideHCID 702EthanolHCID 54009034HCID 54009034, compoundHCID 72720462Ammonium trisulfide

Product 1

HCID 135819067HCID 135819067, compound

Procedure

A solution of 5 g. of ethyl 4-acetoxybenzoyldiazoacetate in 200 ml. of ethanol is treated with 50 ml. of aqueous 20% ammonium polysulfide solution and through the resulting mixture is passed a slow stream of hydrogen sulfide for 4 hours. The precipitate which forms is collected by filtration, dissolved in methylene chloride and filtered through a column of alkaline alumina, eluting the column with methylene chloride and methylene chloride containing increasing percentages of ether. The combined eluates are evaporated to dryness and the residue crystallized from ethyl acetatemethanol, thus obtaining the pure 5-(2-hydroxyphenyl)-4-carboethoxy-1,2,3-thiadiazole.

Workup

  1. customfor 4 hours
  2. filtrationThe precipitate which forms is collected by filtration
  3. dissolutiondissolved in methylene chloride
  4. filtrationfiltered through a column of alkaline alumina
  5. washeluting the column with methylene chloride and methylene chloride containing
  6. temperatureincreasing percentages of ether
  7. customThe combined eluates are evaporated to dryness
  8. customthe residue crystallized from ethyl acetatemethanol

Sources & evidence

ORD record
ord-7319ac52e30e40fea458fb50d97e76a7
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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