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

HRID 522879

반응식

HRID 522879 반응식
[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

참가 물질

4

반응물 3

HCID 63184-Chlorobenzoic AcidHCID 14923Ammonium HydroxideHCID 14878232-Hydrazinopyrazine

생성물 1

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

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-24e9a3bbff2040d09a535fde2c205b07
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334269B2

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