Dimethyl Sulfate → N-Methyl Morpholinium Acetonitrile

HRID 619666Notes

Reaction equation

HRID 619666 reaction equation
[N:1]1([CH2:7]C#N)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S(OC)(OC)(=O)=O>C(OCC)(=O)C>[C:2](#[N:1])[CH3:3].[CH3:7][NH+:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 220554-Morpholineacetonitrile

Product 1

HCID 86752400N-Methyl Morpholinium AcetonitrileYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 30 g of morpholine acetonitrile in 75 ml of ethyl acetate was added 22.5 ml of dimethyl sulfate, corresponding to approximately equivalent molar amounts of the two reagents. The resulting solution was mechanically stirred in an oil bath maintained at 40° C. After 10 minutes of stirring, a semi-solid precipitate having a brownish coloration formed and settled on the bottom of the flask. HPLC (high pressure liquid chromatography) analysis showed at least 4 undesirable side products, which were removed. The remaining solution was again heated to 40° C. and reacted for an additional 16 hours. After this time, the resulting white paste was filtered and washed with ethyl acetate. MMA was isolated after drying this filtrate as a free flowing off-white solid in 79% yield, having a melting point of 99-101° C. The purity of the MMA was determined by HPLC to be greater than 95%.

Workup

  1. stirringAfter 10 minutes of stirring
  2. customformed
  3. customwere removed
  4. temperatureThe remaining solution was again heated to 40° C.
  5. customreacted for an additional 16 hours
  6. filtrationAfter this time, the resulting white paste was filtered
  7. washwashed with ethyl acetate
  8. customMMA was isolated
  9. customafter drying this filtrate as

Sources & evidence

ORD record
ord-bc829b06569b4fba801394715c3add93
Source dataset
uspto-grants-1999_09
Patent number
US05959104

Reaction notes

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