Ethanol → Ethyl [(2-methylacryloyl)amino](oxo)acetate

HRID 1032077Notes

Reaction equation

HRID 1032077 reaction equation
N1[CH:6]=[CH:5]C=CC=1.Cl.[C:8]([C:11]1[O:12][C:13](=[O:17])[C:14](=[O:16])[N:15]=1)([CH3:10])=[CH2:9].C([OH:20])C>>[C:14]([NH:15][C:11](=[O:20])[C:8]([CH3:10])=[CH2:9])([C:13]([O:12][CH2:5][CH3:6])=[O:17])=[O:16]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 1049PyridineHCID 221576152-Isopropenyloxazoline-4,5-dione hydrochloride

Product 1

HCID 14298183Ethyl [(2-methylacryloyl)amino](oxo)acetate

Conditions

Temperature
0 °C

Procedure

In the same reaction vessel as used in Example 1, ethanol (230.4 g; 5.0 mol) and pyridine (39.6 g; 0.5 mol) were charged, and the reaction vessel was cooled at 0° C. in an ice bath. 2-Isopropenyloxazoline-4,5-dione hydrochloride (87.8 g; 0.5 mol) was added thereto in 30 minutes under stirring while keeping the reaction temperature at 0° to 10° C. After completion of the addition, excess ethanol was removed under reduced pressure. The reaction mixture was shaken with ethyl acetate (1,000 ml) and a large amount of water, and the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate, followed by removal of ethyl acetate. Hydroquinone (0.01 g) was added thereto, and distillation under reduced pressure was carried out to give N-ethoxalylmethacrylamide (30.5 g). Yield, 33%.

Workup

  1. additionwere charged
  2. customat 0° to 10° C
  3. customwas removed under reduced pressure
  4. stirringThe reaction mixture was shaken with ethyl acetate (1,000 ml)
  5. customa large amount of water, and the ethyl acetate layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customfollowed by removal of ethyl acetate
  8. additionHydroquinone (0.01 g) was added
  9. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-8d9e55f310f74a7c8dcd9fc0f4bab86d
Source dataset
uspto-grants-1990_09
Patent number
US04956491

Reaction notes

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