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4-Aminobenzamide → N-(4-carbamoylphenyl)-3-(5-phenyl-4-isoxazolyl)propionamide

HRID 1794372
Notes
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Reaction equation

HRID 1794372 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[C:11]1([C:17]2[O:21][N:20]=[CH:19][C:18]=2[CH2:22][CH2:23][C:24](O)=[O:25])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:24](=[O:25])[CH2:23][CH2:22][C:18]2[CH:19]=[N:20][O:21][C:17]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:3][CH:4]=1)(=[O:7])[NH2:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 760794-AminobenzamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 222212543-(5-Phenyl-4-isoxazolyl)propionic acid

Product 1

HCID 22221422N-(4-carbamoylphenyl)-3-(5-phenyl-4-isoxazolyl)propionamideYield 71%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-aminobenzamide (0.55 g), 3-(5-phenyl-4-isoxazolyl)propionic acid (0.87 g), 1-hydroxy-1H-1,2,3-benzotriazole hydrate (0.68 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.88 g) and N,N-dimethylformamide (20 ml) was stirred at room temperature overnight. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate and then saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and N-(4-carbamoylphenyl)-3-(5-phenyl-4-isoxazolyl)propionamide (0.95 g, yield 71%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 250–251° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate
  3. dry with materialsaturated brine, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b6b8e8d3dc404acc8dcc3f6995c8cf96
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07022725B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes