3-Aminobenzamide → 3-{[(4-Bromophenoxy)acetyl]amino}benzamide

HRID 1945386Notes

Reaction equation

HRID 1945386 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH2:19])=[O:18].Cl.C(NCCCN=C=NCC)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH2:19])=[O:18])=[O:10])=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 16453-AminobenzamideHCID 74657p-Bromophenoxyacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 866015281-(3-Ethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Product 1

HCID 173978023-{[(4-Bromophenoxy)acetyl]amino}benzamideYield 21.52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (4-bromo-phenoxyacetic acid (392.5 mg, 1.8 mmol), 3-amino-benzamide (408.2 mg, 3.0 mmol), N-(3-ethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (517.6 mg, 2.7 mmol) and 1-hydroxybenzotriazole (HOBt) (365.3 mg, 2.7 mmol) in DMF (18 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (0.47 ml, 2.7 mmol). The mixture was stirred overnight and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by recrystallization from the mixture of Ethyl acetate and MeOH to give 3-[2-(4-bromo-phenoxy)acetyl-amino]-benzamide as a white solid (134.9 mg, 21.52% yield).

Workup

  1. distillationredistilled (DIPEA) (0.47 ml, 2.7 mmol)
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization from the mixture of Ethyl acetate and MeOH

Sources & evidence

ORD record
ord-2bf3b5ca4dc64704b75dad322be49c28
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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