4-Chlorobenzoic Acid → 3-(4-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyrazine

HRID 522879

反応式

HRID 522879 の反応式
[NH:1]([C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)[NH2:2].[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=O)=[CH:12][CH:11]=1.[OH-].[NH4+]>>[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]2[N:4]3[CH:5]=[CH:6][N:7]=[CH:8][C:3]3=[N:1][N:2]=2)=[CH:12][CH:11]=1

参加物

4

反応物 3

HCID 63184-Chlorobenzoic AcidHCID 14923Ammonium HydroxideHCID 14878232-Hydrazinopyrazine

生成物 1

HCID 673767813-(4-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyrazine

反応条件

温度
110 °C

実験手順

To 2-hydrazinopyrazine (1.60 g, 14.55 mmol) was added 4-chloro-benzoic acid (3 eq) followed by 20 mL of polyphosphoric acid, and the reaction mixture was stirred at 110° C. for 18 h. The hot PPA solution was added to ice and neutralized by the addition of ammonium hydroxide (highly exothermic!). The aqueous solution was extracted with ethyl acetate, washed with brine, and dried over anhydrous sodium sulfate. Concentration followed by flash chromatography (silica gel, 1:1 hexanes: ethyl acetate) afforded 3-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyrazine, as a viscous oil.

後処理

  1. additionThe hot PPA solution was added to ice
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration

出典と根拠

ORDレコード
ord-24e9a3bbff2040d09a535fde2c205b07
出典データセット
uspto-grants-2016_05
特許番号
US09334269B2

関連ノート

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