Acetic Anhydride → HCID 54228403, compound

HRID 1855691Notes

Reaction equation

HRID 1855691 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=[O:7])(=O)[CH3:2].[C:9]([O:12][C:13](=O)C)(=O)[CH3:10].C([O-])(=O)C.[Pb+2].C([O-])(=O)C.COCC=O>O1CCCC1>[CH3:13][O:12][CH2:9][CH:10]=[C:5]1[C:6](=[O:7])[O:8][C:1]([CH3:2])=[N:4]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 9317Lead diacetateHCID 10972AcetylglycineHCID 91563Methoxyacetaldehyde

Product 1

HCID 54228403HCID 54228403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask equipped with a mechanical stirrer, reflux condenser, dropping funnel, and drying tube was charged with 38.5 g (0.33 mol) of N-acetylglycine (2), 134 g (1.3 mol) of acetic anhydride, 54 g (0.166 mol) of lead acetate, and 450 ml of tetrahydrofuran (THF). The mixture was heated with stirring at reflux temperature for 1 hr. A solution consisting of 37 g (0.5 mol) of methoxyacetaldehyde (1) and 220 ml of THF was then added dropwise over a 21/2 hr period. The resultant mixture was heated with stirring at reflux temperature for an additional 4 hrs. The reaction was allowed to cool, diluted with 1 l. of ether, and filtered through a pad of Celite®. The filtrate was concentrated in vacuo and the dark brown fluid residue was distilled under reduced pressure. The fraction boiling at 60°-83°/0.5 mm consisted mainly of 4-(2-methoxyethylidene)-2-methyl-5-oxazolone (3): NMR (CDCl3) δ 6.5 (m, 1H, --CH2CH=), 4.35 (m, 2H, --CH2CH--), 3.3 (s, 3H, CH3O--), 2.2 ##STR5##

Workup

  1. customA flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. customdrying tube
  4. temperatureThe mixture was heated
  5. temperatureat reflux temperature for 1 hr
  6. additionwas then added dropwise over a 21/2 hr period
  7. stirringwith stirring
  8. temperatureat reflux temperature for an additional 4 hrs
  9. temperatureto cool
  10. additiondiluted with 1 l
  11. filtrationof ether, and filtered through a pad of Celite®
  12. concentrationThe filtrate was concentrated in vacuo
  13. distillationthe dark brown fluid residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-ffba666e2a9848889ac85d1fc6f5fab1
Source dataset
uspto-grants-1980_08
Patent number
US04216008

Reaction notes

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