Pentane → 2-[1,2,4-Triazolo(4,3-a)pyridin-3-ylmercapto]ethanol

HRID 476908Notes

Reaction equation

HRID 476908 reaction equation
[SH:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:18][CH2:19][OH:20].CCCCC>C(O)C>[N:4]1[N:3]=[C:2]([S:1][CH2:18][CH2:19][OH:20])[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

6

Reactant 4

HCID 8003PentaneHCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 178527925HCID 178527925, compound

Product 1

HCID 198371042-[1,2,4-Triazolo(4,3-a)pyridin-3-ylmercapto]ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

60 g of 3-mercapto-1,2,4-triazolo(4,3-a)pyridine are dissolved in 500 ml of ethanol. 21 g of sodium carbonate and 29 ml of 2-bromoethanol are then added. The reaction mixture is heated under reflux for 9 hours, the mineral substances are filtered off, the filtrate is then concentrated in vacuo, the concentrate is taken up with water acidified with 0.5N hydrochloric acid and extraction is carried out with chloroform. The aqueous phase is then rendered basic with aqueous ammonia, saturated with sodium chloride and then extracted with chloroform. The chloroform phase obtained is dried over magnesium sulfate and then concentrated in vacuo. The crystals which then form are taken up with pentane, filtered off, washed with pentane and dried to give 69.2 g of 2-[1,2,4-triazolo(4,3-a)pyridin-3-ylmercapto]ethanol in the form of crystals melting at 84° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 9 hours
  3. filtrationthe mineral substances are filtered off
  4. concentrationthe filtrate is then concentrated in vacuo
  5. extractionacidified with 0.5N hydrochloric acid and extraction
  6. extractionextracted with chloroform
  7. customThe chloroform phase obtained
  8. dry with materialis dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crystals which then form
  11. filtrationfiltered off
  12. washwashed with pentane
  13. customdried

Sources & evidence

ORD record
ord-47f4155105a94457bd691a6bace892f8
Source dataset
uspto-grants-1989_12
Patent number
US04886805

Reaction notes

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