1,1'-Carbonyldiimidazole → HCID 19092317, compound

HRID 257772Notes

Reaction equation

HRID 257772 reaction equation
[NH2:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:5].[C:30](N1C=CN=C1)(N1C=CN=C1)=[O:31]>O1CCCC1>[N+:27]([C:25]1[CH:26]=[C:2]2[C:3]([C:4](=[O:5])[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][N:11]3[CH2:12][CH:13]=[C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:15][CH2:16]3)[C:30](=[O:31])[NH:1]2)=[CH:23][CH:24]=1)([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 19092314HCID 19092314, compound

Product 1

HCID 19092317HCID 19092317, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-4-nitro-N-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]benzamide (0.52 g) and carbonyldiimidazole (0.43 g) in dry tetrahydrofuran (10 ml) was stirred under reflux for 2 hours. After evaporation of the solvent, the crude residue was crystallized and recrystallized from ethanol to give crystals of 7-nitro-3-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-1,2,3,4-tetrahydroquinazoline-2,4-dione (0.32 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. customAfter evaporation of the solvent
  3. customthe crude residue was crystallized
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ea538808c21d47a5a6f34b5b47707b66
Source dataset
uspto-grants-1993_11
Patent number
US05264438

Reaction notes

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