1,1'-Carbonyldiimidazole → HCID 22936848, compound

HRID 853251Notes

Reaction equation

HRID 853251 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[NH2:30])=[CH:18][CH:17]=1.[C:31](N1C=CN=C1)(N1C=CN=C1)=[O:32]>CN(C)C=O.O1CCCC1.O>[NH:30]1[C:25]2[C:24](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][N:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:21][CH:20]=2)[C:31]1=[O:32]

Participants

6

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22936325HCID 22936325, compound

Product 1

HCID 22936848HCID 22936848, compoundYield 7.05%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

6,7-Dimethoxy-4-(4-(2-aminophenyl)methylaminophenyloxy)quinoline (40 mg, 0.0996 mmol) was dissolved in dimethylformamide (0.5 ml), 1,1′-carbonyldiimidazole (19 mg, 0.1196 mmol) was added, and the mixture was stirred at 70° C. for 8 hours. After cooling to room temperature, the reaction solution was diluted with tetrahydrofuran, water was added, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure. The residue was purified with a silica gel column (ethyl acetate-methanol system) and recrystallized with hexane-diethyl ether to obtain the title compound (3 mg, 0.0070 mmol, 7.05%) as colorless crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationafter which the solvent was distilled off under reduced pressure
  7. customThe residue was purified with a silica gel column (ethyl acetate-methanol system)
  8. customrecrystallized with hexane-diethyl ether

Sources & evidence

ORD record
ord-aecd06605567440ea49ff936f4dd22fc
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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