Sodium Methoxide → HCID 178420904, compound

HRID 1032904Notes

Reaction equation

HRID 1032904 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([SH:6])=[N:2]1.C[O-].[Na+].CS(O[CH2:15][CH:16]1[CH2:19][CH2:18][CH2:17]1)(=O)=O>CO>[NH:1]1[CH:5]=[N:4][C:3]([S:6][CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)=[N:2]1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 22381912HCID 22381912, compoundHCID 178527894HCID 178527894, compound

Product 1

HCID 178420904HCID 178420904, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1,2,4-triazole-3-thiol (20.2 g; 0.20 mol) and sodium methoxide (11.8 g; 0.22 mol) in methanol (250 ml) is added cyclobutylmethyl methanesulfonate (36.4 g; 0.22 mol). The mixture was refluxed for 27 h under dry nitrogen, allowed to cool to 25° C. and filtered. The solid was washed with ethyl acetate and the organic solutions combined and evaporated. The residue was dissolved in water (250 ml) and extracted into ethyl acetate (250 ml) and dichloromethane (100 ml). The extracts were combined, dried (Na2SO4), filtered and evaporated to afford crude cyclobutylmethyl 1,2,4-triazol-3-yl sulfide (21.8 g; 65%) as a white, sticky solid. NMR -d(CDCl3 ; 60 MHz) 1.5-2.8 (m), 3.2 (2H, d, J=7 Hz), 8.0 (1H, s) and 12.4 (1H, br s).

Workup

  1. temperatureThe mixture was refluxed for 27 h under dry nitrogen
  2. filtrationfiltered
  3. washThe solid was washed with ethyl acetate
  4. customevaporated
  5. dissolutionThe residue was dissolved in water (250 ml)
  6. extractionextracted into ethyl acetate (250 ml) and dichloromethane (100 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-c996e7cab2b0468299c28b96d974e63a
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

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