Acetic Acid → 4-Ethyl-3-(methylsulfonyl)-5-(2-thienyl)-4H-1,2,4-triazole

HRID 732032Notes

Reaction equation

HRID 732032 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[N:6][N:5]=[C:4]1[S:13][CH3:14])[CH3:2].OO.[OH-:17].[Na+].C(O)(=[O:21])C>>[CH2:1]([N:3]1[C:7]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[N:6][N:5]=[C:4]1[S:13]([CH3:14])(=[O:21])=[O:17])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 45095579HCID 45095579, compound

Product 1

HCID 473318934-Ethyl-3-(methylsulfonyl)-5-(2-thienyl)-4H-1,2,4-triazoleYield 60%

Procedure

The title compound was synthesized according to the method described in Åkerblom et al. J. Med. Chem. 16, 312 (1973). 4-Ethyl-3-methylsulfanyl-5-thiophen-2-yl-4H-[1,2,4]triazole (1.14 g, 5.06 mmol) was dissolved in glacial acetic acid (20 ml) followed by the addition of 30% hydrogen peroxide (5 ml). After stirring at ambient temperatures for 16 h additional 30% hydrogen peroxide (5 ml) was added. The mixture was stirred for 3 h at ambient temperature, then heated to 100° C. for 2.5 h. After cooling in an ice/water bath the reaction was neutralized with sodium hydroxide and extracted twice with dichloromethane. The organic layers were combined, evaporated to dryness and dried in vacuo yielding the title compound (0.78 g, 60%). 1H NMR (CDCl3), δ (ppm): 7.60 (d, 1H), 7.56 (d, 1H), 7.22 (m, 1H), 4.51 (q, 2H), 3.58 (s, 3H), 1.55 (t, 3H).

Workup

  1. customThe title compound was synthesized
  2. additionwas added
  3. temperatureheated to 100° C. for 2.5 h
  4. temperatureAfter cooling in an ice/water bath the reaction
  5. extractionextracted twice with dichloromethane
  6. customevaporated to dryness
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1709b844c380439eaa0a32af6cb25a10
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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