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Hydrochloric Acid → N-(2-fluoroethyl)-N-methyloxamic acid

HRID 45307
Notes
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Reaction equation

HRID 45307 reaction equation
[CH3:1]O.[OH-].[Na+].Cl.[F:6][CH2:7][CH2:8][N:9](NC)[C:10](=[O:14])[C:11]([OH:13])=[O:12]>O>[F:6][CH2:7][CH2:8][N:9]([CH3:1])[C:10](=[O:14])[C:11]([OH:13])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86661508N-(2-fluoroethyl)-N-methylaminooxamic acid

Product 1

HCID 55301814N-(2-fluoroethyl)-N-methyloxamic acidYield 66%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a mixed solvent comprising 6 ml of methanol and 5 ml of water, there was suspended 1.56 g of N-(2-fluoroethyl)-N-methylmethoxyoxalylamide, then 3.2 g of a 15% aqueous solution of sodium hydroxide was dropwise added, with ice-cooling, to the suspension and then the mixture was stirred for one hour. Concentrated hydrochloric acid was added to the reaction system, the mixture was then extracted with ethyl acetate, the organic phase thus separated was washed with water, dried over magnesium sulfate and then the ethyl acetate was distilled off from the organic phase to thus give, as the target product, 0.94 g (yield: 66%, a solid product) of N-(2-fluoroethyl)-N-methylaminooxamic acid.

Workup

  1. temperaturecooling, to the suspension
  2. extractionthe mixture was then extracted with ethyl acetate
  3. customthe organic phase thus separated
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe ethyl acetate was distilled off from the organic phase
  7. customto thus give, as the target product, 0.94 g (yield: 66%

Sources & evidence

ORD record
ord-d44f2c5488034fda8a8f1830b69e4112
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541473B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes