1,1'-Carbonyldiimidazole → HCID 178486835, compound

HRID 1351169Notes

Reaction equation

HRID 1351169 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[N:9]=[CH:8][N:7]=[C:6]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[C:4]=1[NH2:22].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>ClCCCl>[CH3:14][O:13][C:12]1[CH:11]=[C:10]2[C:5]3[C:6]([N:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:23](=[O:24])[NH:22][C:4]=3[C:3]=1[O:2][CH3:1])=[N:7][CH:8]=[N:9]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21098395HCID 21098395, compound

Product 1

HCID 178486835HCID 178486835, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6,7-dimethoxy-N4-phenyl-quinazoline-4,5-diamine (0.2 g, 0.68 mmol) (from Example 1, Step C, supra) in 1,2-dichloroethane (50 mL) was added 1,1′-carbonyldiimidazole (0.55 g, 3.4 mmol) (Aldrich). The reaction mixture was heated with stirring at 90° C. for 4 hours. The solvent was evaporated and the residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (1:1:0.04) as eluent to give the desired 8,9-dimethoxy-3-phenyl-1H,3H-1,3,4,6-tetraaza-phenalen-2-one as a yellow solid. (Yield 0.13 g, 59%).

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-07d00d992bd04b20b517941f3a749570
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

Loading…