Isatoic Anhydride → HCID 28267823, compound

HRID 1846280Notes

Reaction equation

HRID 1846280 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]12[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14]C(=O)O[C:10]2=[O:11]>CN(C)C=O.C(OCC)(=O)C>[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=1[C:10]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)=[O:11]

Participants

5

Reactant 2

HCID 8359Isatoic AnhydrideHCID 108934-Iodoaniline

Product 1

HCID 28267823HCID 28267823, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 4-iodoaniline (4.03 g, 18.4 mmol) in N,N-dimethylformamide (20 mL) was added isatoic anhydride (3.00 g, 18.4 mmol), and the reaction mixture was heated at 115° C. for 14 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 mL). The organic layer was washed with 1 N NaOH (200 mL), water (100 mL), then brine, and dried over Na2SO4. The solvent was removed under reduced pressure to give crude product, which was purified by column chromatography (silica gel 230-400 mesh; 10% EtOAc/hexane as eluent) to give 2-amino-N-(4-iodo-phenyl)-benzamide as white solid. Yield: 1.50 g (24%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with 1 N NaOH (200 mL), water (100 mL)
  3. dry with materialbrine, and dried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customto give crude product, which
  6. customwas purified by column chromatography (silica gel 230-400 mesh; 10% EtOAc/hexane as eluent)

Sources & evidence

ORD record
ord-062b25c79b5c4f74bc6b4cf772456db1
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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