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Phosphorus oxychloride → 3-Formyl-2-methyl-8-nitro-imidazo[1,2-a]pyridine

HRID 1195738
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인쇄 미리보기

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HRID 1195738 반응식
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1[N:8]=[C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]2[CH:18]=1.[C:19](=O)([O-])[OH:20].[Na+]>CN(C)C=O>[CH:19]([C:18]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:9]2=[N:8][C:7]=1[CH3:6])=[O:20]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychloride2회HCID 516892Sodium BicarbonateHCID 218273482-Methyl-8-nitroimidazo[1,2-a]pyridine

생성물 1

HCID 541686243-Formyl-2-methyl-8-nitro-imidazo[1,2-a]pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

20 ml phosphoroxychloride is added dropwise within 5 minutes to a solution of 7.6 g 2-methyl-8-nitro-imidazo[1,2-a]pyridine in 100 ml dimethylformamide at 0° C. After stirring for 1 hour at 0° C. and for 2 hours at 70° C. the mixture is cooled again to 0° C. 10 ml phosphoroxychloride is added dropwise and the same procedure is carried out as before. When the reaction is finished the mixture is poured over 200 ml icewater, neutralized with saturated sodium hydrogen carbonate solution and extracted 3×with 50 ml ethyl acetate each time. The solvent is stripped off in vacuo and the residue is washed with ether and recrystallized from acetronitrile, giving the title compound of m.p. 188°-189° C.

후처리

  1. temperatureis cooled again to 0° C
  2. additionis poured over 200 ml icewater
  3. extractionextracted 3×with 50 ml ethyl acetate each time
  4. washthe residue is washed with ether
  5. customrecrystallized from acetronitrile

출처 및 근거

ORD 기록
ord-7b230e6d684945e29c5c39dd437c2c9a
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05112834

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