Sodium Methoxide → HCID 178420905, compound

HRID 1032906Notes

Reaction equation

HRID 1032906 reaction equation
[CH:1]1([CH2:6]Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:8]1[CH:12]=[N:11][C:10]([SH:13])=[N:9]1.C[O-].[Na+]>CO>[NH:8]1[CH:12]=[N:11][C:10]([S:13][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:9]1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12723264(Bromomethyl)cyclopentaneHCID 178527894HCID 178527894, compound

Product 1

HCID 178420905HCID 178420905, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopentylmethyl bromide (21 g; 0.13 mol) was added in one portion to 1,2,4-triazole-3-thiol (12.3 g; 0.12 mol) and sodium methoxide (7.1 g; 0.13 mol) in dry methanol (100 ml) under dry nitrogen. The mixture was stirred at room temperature for 3 days, refluxed for 3 h and evaporated. The residue was dissolved in ethyl acetate (200 ml) and water (100 ml), the organic phase separated, washed with water (100 ml), dried (Na2SO4), filtered and evaporated, to afford cyclopentylmethyl 1,2,4-triazol-3-yl sulfide (18.1 g; 82%) as a waxy, off-shite solid, m.p. 48°-55° C.

Workup

  1. temperaturerefluxed for 3 h
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (200 ml)
  4. customwater (100 ml), the organic phase separated
  5. washwashed with water (100 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-19766ef4ac3340eda100fabbae66fa29
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

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