Isatoic Anhydride → 2-amino-N-[1-(4-chloro-phenyl)-ethyl]-benzamide

HRID 388483Notes

Reaction equation

HRID 388483 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCOC(C)=O>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:22][CH:20]([C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)[CH3:21])=[O:4]

Participants

6

Reactant 3

HCID 8359Isatoic AnhydrideHCID 81531DiisopropylethylamineHCID 978031-(4-Chlorophenyl)ethylamine

Product 1

HCID 174435132-amino-N-[1-(4-chloro-phenyl)-ethyl]-benzamideYield 14%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of isatoic anhydride (500 mg, 3.07 mmol) and 1-(4-chloro-phenyl)-ethylamine (530 mg, 3.68 mmol) in CH2Cl2 (20 mL) is added diisopropyl ethyl amine (1.2 mL, 6.89 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with EtOAc (100 mL) and is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, concentrated and the resulting residue is purified by flash chromatography with 25% EtOAc in Hexane as the eluent to afford the desired to afford the desired 2-amino-N-[1-(4-chloro-phenyl)-ethyl]-benzamide (115 mg, 14%).

Workup

  1. washis washed with H2O (50 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue is purified by flash chromatography with 25% EtOAc in Hexane as the eluent
  5. customto afford the

Sources & evidence

ORD record
ord-c0ba892d8361423ebdc742457cacb78f
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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