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

HRID 1456055Notes

Reaction equation

HRID 1456055 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]benzamide

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°-2070° 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-aad48d5bd6df4783a580bd7ec94c4f6f
Source dataset
uspto-grants-1998_12
Patent number
US05843944

Reaction notes

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