Ethanol → HCID 21557567, compound

HRID 1579059Notes

Reaction equation

HRID 1579059 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][S:11][C:12]=1[C:13]([O:15]CC)=[O:14].C(O)C.[OH-].[Na+]>O>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][S:11][C:12]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21557578HCID 21557578, compound

Product 1

HCID 21557567HCID 21557567, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 10 g. of 4-(2-hydroxyphenyl)5-carboethoxy-1,2,3-thiadiazole in 500 ml. of ethanol is added a solution of 5 g. of sodium hydroxide in 25 ml. of water. The reaction mixture is refluxed for 4 hours and then evaporated to a small volume under vacuo. It is then cooled, diluted with water and extracted with ether to eliminate unsaponifiable products. The aqueous phase is acidified with 10% hydrochloric acid solution and extracted with ethyl acetate. The combined ethyl acetate extracts are washed with sodium chloride solution, dried over sodium sulfate and evaporated to dryness under vacuo. Crystallization of the residue from ethyl acetate-methanol, affords the pure 4-(2-hydroxyphenyl)5-carboxy-1,2,3-thiadiazole.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customevaporated to a small volume under vacuo
  3. temperatureIt is then cooled
  4. additiondiluted with water
  5. extractionextracted with ether
  6. extractionextracted with ethyl acetate
  7. washThe combined ethyl acetate extracts are washed with sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customevaporated to dryness under vacuo
  10. customCrystallization of the residue from ethyl acetate-methanol

Sources & evidence

ORD record
ord-42d660af06a7403a94d4b262a1505406
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

Loading…