Acetohydroxamic Acid → Caracemide

HRID 1648762Notes

Reaction equation

HRID 1648762 reaction equation
[C:1]([NH:4][OH:5])(=[O:3])[CH3:2].[CH3:6][N:7]=[C:8]=[O:9]>C(N(CC)CC)C.C(Cl)Cl>[CH3:6][NH:7][C:8]([N:4]([O:5][C:8]([NH:7][CH3:6])=[O:9])[C:1](=[O:3])[CH3:2])=[O:9]

Participants

5

Reactant 2

HCID 1990Acetohydroxamic AcidHCID 12228Methyl Isocyanate

Product 1

HCID 54747Caracemide

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of acetohydroxamic acid (7.5 grams), methyl isocyanate (12.0 grams), 80 milliliters (ml) of methylene chloride, and about three drops of triethylamine were stirred together for about one hour in order to obtain solution. The solution was allowed to stand at room temperature overnight after which the solvent was removed under vacuum, leaving a residue. The residue was recrystallized from methylene chloride leaving the desired N-((methylamino)carbonyl)-N-(((methylamino)carbonyl)oxy)acetamide as white crystals having a melting point (m.p.) of 121°-123.5° C.

Workup

  1. customto obtain solution
  2. waitto stand at room temperature overnight
  3. customafter which the solvent was removed under vacuum
  4. customleaving a residue
  5. customThe residue was recrystallized from methylene chloride leaving the desired N-((methylamino)carbonyl)-N-(((methylamino)carbonyl)oxy)acetamide as white crystals
  6. customa melting point (m.p.) of 121°-123.5° C.

Sources & evidence

ORD record
ord-bda5ec0b37944ff997791b0f58c60577
Source dataset
uspto-grants-1983_11
Patent number
US04413009

Reaction notes

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