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

HRID 732032ノート

反応式

HRID 732032 の反応式
[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]

参加物

5

反応物 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2 回HCID 14798Sodium HydroxideHCID 450955794-ethyl-3-(methylthio)-5-(thiophen-2-yl)-4H-1,2,4-triazole

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1709b844c380439eaa0a32af6cb25a10
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

反応ノート

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