1,1'-Carbonyldiimidazole → 2-Methyl-N-[4-(pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]benzamide

HRID 3498

반응식

HRID 3498 반응식
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)=[O:5].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:32]1[N:36]2[C:37]3[C:42]([NH:43][CH2:44][C:35]2=[CH:34][CH:33]=1)=[CH:41][CH:40]=[CH:39][CH:38]=3>O1CCCC1>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([N:43]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]3[CH:32]=[CH:33][CH:34]=[C:35]3[CH2:44]2)=[O:12])=[CH:9][CH:8]=1)=[O:5]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 107074414-[(2-methylbenzoyl)amino]benzoyl ChlorideHCID 118051814,5-Dihydropyrrolo[1,2-a]quinoxaline

생성물 1

HCID 153406682-Methyl-N-[4-(pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]benzamide수율 34.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 0.51 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride and 0.36 g of 1,1'-carbonyldiimidazole in 6 ml of tetrahydrofuran is stirred at room temperature for 1 hour. To the reaction mixture is added 0.17 g of 4,5-dihydropyrrolo-[1,2-a]-quinoxaline followed by heating at reflux for 60 hours. The volatiles are concentrated in vacuo to a residue which is dissolved in ethyl acetate. The organic layer is washed with 1N HCl, 1M NaHCO3, brine, dried with Na2SO4 and filtered through hydrous magnesium silicate. The volatiles are concentrated in vacuo to a residue which is chromatographed by elution with 1:2 ethyl acetate-hexanes to give 0.14 g of the desired product as a white solid, m.p. 206°-207° C.;

후처리

  1. temperatureby heating
  2. temperatureat reflux for 60 hours
  3. concentrationThe volatiles are concentrated in vacuo to a residue which
  4. dissolutionis dissolved in ethyl acetate
  5. washThe organic layer is washed with 1N HCl, 1M NaHCO3, brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered through hydrous magnesium silicate
  8. concentrationThe volatiles are concentrated in vacuo to a residue which
  9. customis chromatographed by elution with 1:2 ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-0f8be2da1ade4ec08c800b2739b8b3df
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733905

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