Ethylamine → HCID 22221021, compound

HRID 1794360Notes

Reaction equation

HRID 1794360 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12][CH2:13][C:14]([OH:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([N:19](CC)CC)[CH3:18].C(Cl)(=O)OCC.C(N)C>O.O1CCCC1>[CH2:17]([NH:19][C:14](=[O:16])[CH2:13][CH2:12][C:8]1[CH:9]=[N:10][O:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:18]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 222212543-(5-Phenyl-4-isoxazolyl)propionic acid

Product 1

HCID 22221021HCID 22221021, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a mixture of 3-(5-phenyl-4-isoxazolyl)propionic acid (1.00 g), triethylamine (1.0 ml) and tetrahydrofuran (50 ml) was added ethyl chlorocarbonate (0.5 ml) at −30° C. and the mixture was stirred at −20° C. for 1 hr. To the obtained mixture was added aqueous ethylamine solution (10 ml), and the mixture was stirred at room temperature for 1 hr. 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 to give N-ethyl-3-(5-phenyl-4-isoxazolyl)propionamide (0.93 g, yield 83%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 75–76° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate
  4. dry with materialsaturated brine, dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3920085449d84e8ca80a5b8bdb26c272
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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