Formaldehyde → HCID 13539135, compound

HRID 2210002Notes

Reaction equation

HRID 2210002 reaction equation
[CH3:1][NH:2][CH2:3]C(O)=O.[CH2:7]=O.[C:9]([O:17][CH3:18])(=[O:16])/[CH:10]=[CH:11]\[C:12]([O:14][CH3:15])=[O:13].O>C1C=CC=CC=1>[CH3:15][O:14][C:12]([C@H:11]1[C@@H:10]([C:9]([O:17][CH3:18])=[O:16])[CH2:7][N:2]([CH3:3])[CH2:1]1)=[O:13]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 1088SarcosineHCID 5271565Dimethyl maleate

Product 1

HCID 13539135HCID 13539135, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 89.0 gm (1.0 mole) N-methylglycine, 60.0 gm (2.0 mole) paraformaldehyde and 144 gm (1.0 mole) dimethyl maleate in 1 L of benzene were heated to reflux with constant water removal for about 5 hours. The reaction mixture was cooled to ambient and allowed to stand over night. The solution was decanted from the solid and the solid was washed with diethyl ether. The combined organic phases were extracted with 10% hydrochloric acid and then this aqueous phase was made basic with concentrated ammonium hydroxide. The now basic aqueous phase was extracted with dichloromethane and the organic extracts were then dried over sodium sulfate and concentrated in vacuo to give a yellow liquid. This material was fractionated through a Vigreaux column to give 74.25 gm of the desired compound, b.p.=119°-123° C. (8 mm Hg).

Workup

  1. temperaturewere heated
  2. temperatureThe reaction mixture was cooled to ambient and
  3. waitto stand over night
  4. customThe solution was decanted from the solid
  5. washthe solid was washed with diethyl ether
  6. extractionThe combined organic phases were extracted with 10% hydrochloric acid
  7. extractionThe now basic aqueous phase was extracted with dichloromethane
  8. dry with materialthe organic extracts were then dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto give a yellow liquid

Sources & evidence

ORD record
ord-52e51b42e9b24899ae9cb8e0b20700c4
Source dataset
uspto-grants-1995_10
Patent number
US05457121

Reaction notes

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