Ethyl isocyanate → N-(Ethylcarbamoyl)-N-[(ethylcarbamoyl)oxy]propanamide

HRID 1648765Notes

Reaction equation

HRID 1648765 reaction equation
[C:1]([NH:5][OH:6])(=[O:4])[CH2:2][CH3:3].[CH2:7]([N:9]=[C:10]=[O:11])[CH3:8]>C(N(CC)CC)C.C(Cl)Cl>[CH2:7]([NH:9][C:10]([N:5]([O:6][C:10]([NH:9][CH2:7][CH3:8])=[O:11])[C:1](=[O:4])[CH2:2][CH3:3])=[O:11])[CH3:8]

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 75743Propionohydroxamic acid

Product 1

HCID 13228807N-(Ethylcarbamoyl)-N-[(ethylcarbamoyl)oxy]propanamide

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

Propiohydroxamic acid (4.5 grams), ethyl isocyanate (8.0 grams), and a few drops of triethylamine were added to 100 ml of methylene chloride and allowed to stand at room temperature for about 12 hours. The solvent was then removed under vacuum leaving a residue which was recrystallized from a solution of methylene chloride and hexane leaving the desired, N-((ethylamino)carbonyl)-N-(((ethylamino)carbonyl)oxy)propionamide as white crystals, m.p. 104°-106° C.

Workup

  1. customThe solvent was then removed under vacuum
  2. customleaving a residue which
  3. customwas recrystallized from a solution of methylene chloride and hexane leaving the

Sources & evidence

ORD record
ord-927f6c10ae484f9babd8e38cfc30aa76
Source dataset
uspto-grants-1983_11
Patent number
US04413009

Reaction notes

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