Acetic Acid → HCID 18937850, compound

HRID 357524Notes

Reaction equation

N1C=C[CH:4]=[CH:3][CH:2]=1.[NH2:7]/[C:8](=[C:14](\Cl)/[C:15]([O:17][CH2:18][CH3:19])=[O:16])/[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:21](O)(=[O:23])C>>[CH3:21][O:23][C:3]1[CH:4]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:7][CH:2]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 1049Pyridine

HCID 14745921HCID 14745921, compound

Product 1

HCID 18937850HCID 18937850, compound

Procedure

83 g (1.05 mol) of pyridine were added to 221.5 g (1.0 mol) of diethyl 2-amino-3-chloromaleate in 250 ml of glacial acetic acid at 80° C. while stirring. 90 g (1.05 mol) of mathoxyacrolein were then added at 120° C. in the course of 30 minutes, gentle refluxing being established without heating. The reaction mixture was stirred for 3 hours at 120° C. and then evaporated down under reduced pressure, water was added to the residue and the mixture was extracted with methylene chloride. After filtration of active carbon, drying, filtration over neutral alumina with suction and evaporating down under reduced pressure, 190 g (75% of theory) of the title compound were obtained as a pale yellow syrup.

Workup

addition90 g (1.05 mol) of mathoxyacrolein were then added at 120° C. in the course of 30 minutes
temperaturegentle refluxing
temperaturewithout heating
stirringThe reaction mixture was stirred for 3 hours at 120° C.
customevaporated down under reduced pressure, water
additionwas added to the residue
extractionthe mixture was extracted with methylene chloride
filtrationAfter filtration of active carbon
customdrying
filtrationfiltration over neutral alumina with suction
customevaporating down under reduced pressure, 190 g (75% of theory) of the title compound
customwere obtained as a pale yellow syrup

Sources & evidence

ORD record: ord-a712cee4d1004bf380dbe7956e88e9fe
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840904

Reaction notes

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