Sodium Carbonate → N-Hydroxy-N-methylhexanamide

HRID 1720450Notes

Reaction equation

HRID 1720450 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH3:16][NH:17][OH:18]>CO>[CH3:16][N:17]([C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[OH:18]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67340Hexanoyl chlorideHCID 77906N-methylhydroxylamine hydrochloride

Product 1

HCID 128286N-Hydroxy-N-methylhexanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hexanoylchloride (g, 0.1 mole) is added dropwise with stirring and ice-cooling to a mixture of sodium carbonate (10.6 g, 0.1 mole) and N-methylhydroxylamine hydrochloride (8.35 g, 0.1 mole) in methanol (60 ml), the temperature being kept at less than 5° C. After stirring for a further 30 minutes the mixture is filtered and the solvent is removed using a rotary evaporator. The resultant residue is re-filtered and the residue distilled in vacuo to yield N-methyl-hexanohydroxamic acid as an oil, b.p. 87°-90°/0.1 mm.

Workup

  1. custombeing kept at less than 5° C
  2. stirringAfter stirring for a further 30 minutes the mixture
  3. filtrationis filtered
  4. customthe solvent is removed
  5. customa rotary evaporator
  6. filtrationThe resultant residue is re-filtered
  7. distillationthe residue distilled in vacuo

Sources & evidence

ORD record
ord-8f75e4f3b2794e88bc1b55b53bed7607
Source dataset
uspto-grants-1996_04
Patent number
US05506266

Reaction notes

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