Acetohydroxamic Acid → Caracemide
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
Product 1
Reagents, catalysts & solvents 2
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
- customto obtain solution
- waitto stand at room temperature overnight
- customafter which the solvent was removed under vacuum
- customleaving a residue
- customThe residue was recrystallized from methylene chloride leaving the desired N-((methylamino)carbonyl)-N-(((methylamino)carbonyl)oxy)acetamide as white crystals
- 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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