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

HRID 55148

Reaction equation

HRID 55148 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 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 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-662f6321882140b28a27444553afc4a9
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Linked notes

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