Butylamine → N-butyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanamide

HRID 486989Notes

Reaction equation

HRID 486989 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13]CC)=O)=[C:4]([CH3:17])[CH:3]=1.[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21]>O.C(O)C>[CH2:18]([NH:22][C:11](=[O:13])[CH2:10][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:17])=[O:16])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 8007ButylamineHCID 14150214Ethyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoate

Product 1

HCID 19096836N-butyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanamideYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.90 grams (0.02 mole) of ethyl 3-[(4-bromo-2-methylphenyl)amino]-3oxopropanoate prepared in Example I (Compound No. 75), 358 grams (4.9 moles) of n-butylamine, 150 milliliters of ethanol and 5 drops of water was stirred at room temperature for about 16 hours. After this period, rotary evaporation gave a crude product as a white solid. The white solid was recrystallized from ethyl acetate-hexane to give 3.08 grams (0.009 mole) of N-butyl 3-[(4-bromo-2-methylphenyl)amino]-3- oxopropanamide having a melting point of 123° C.-125° C. Elemental analysis of the product indicated the following:

Workup

  1. waitAfter this period
  2. customrotary evaporation
  3. customgave a crude product as a white solid
  4. customThe white solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-af79c5036dff4a4f9b75687d1c849f33
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Reaction notes

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