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

HRID 1419967Notes

Reaction equation

HRID 1419967 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.;

Workup

  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

Sources & evidence

ORD record
ord-fb9a67011f4c46b18eadcf28d6c2b653
Source dataset
uspto-grants-1999_03
Patent number
US05889001

Reaction notes

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