Acetic Anhydride → HCID 22132733, compound

HRID 1857283Notes

Reaction equation

HRID 1857283 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:40](OC(=O)C)(=[O:42])[CH3:41].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:40]([O:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:16][CH:17]=2)=[O:10])=[CH:4][CH:3]=1)(=[O:42])[CH3:41]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22132675HCID 22132675, compound

Product 1

HCID 22132733HCID 22132733, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Hydroxyphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea (47 mg) was dissolved in methylene chloride (6 ml), after the addition of triethylamine (2 ml), acetic anhydride (0.5 ml) was added, and the admixture was stirred at room temperature for 15 hours. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 35 mg of the title compound (yield: 68%).

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted 2 times with ethyl acetate
  3. washthe organic layer was then washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was removed by reduced-pressure distillation
  6. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-9ecb5927567b477883396de43288939a
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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