Benzene → HCID 54445307, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][N+:6]#[C-:7])[CH3:2].[O:9]=[CH:10][C:11](=[CH2:13])C.[CH:14]1C=CC=CC=1>[Cu-]=O>[CH2:1]([O:3][C:4]([CH:5]1[CH:10]([CH2:11][CH:13]=[CH2:14])[O:9][CH:7]=[N:6]1)=[O:8])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1.6 g of red copper(1) oxide are introduced into 200 ml of benzene. A solution of 140 g of isocyanoacetic acid ethyl ester and 105 g of freshly distilled methacrolein in 200 ml of benzene is added dropwise to this suspension within a period of 10 minutes with vigorous stirring, during which time the reaction temperature is kept at between 30° and 32° by cooling with ice. When the addition is complete, the mixture is kept at 30°-32° until the exothermic reaction subsides, and is then stirred at room temperature for one hour. After excess copper(I) oxide has been filtered off, the filtrate is concentrated by evaporation in vacuo at 30°. 600 ml of ether are added to the residue, which is then filtered over Celite and concentrated to dryness by evaporation in vacuo. In this manner, 5-(2-propenyl)-2-oxazoline-4-carboxylic acid ethyl ester is obtained in the form of a colourless oil having a boiling point of 110°-130° (5.3 Pa).
Workup
- customis kept at between 30° and 32°
- temperatureby cooling with ice
- additionWhen the addition
- customthe mixture is kept at 30°-32° until the exothermic reaction subsides
- filtrationAfter excess copper(I) oxide has been filtered off
- concentrationthe filtrate is concentrated by evaporation in vacuo at 30°
- addition600 ml of ether are added to the residue, which
- filtrationis then filtered over Celite
- concentrationconcentrated to dryness by evaporation in vacuo
Sources & evidence
- ORD record
- ord-f2f628210deb4335b01bb3dea729fe68
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05175344
Reaction notes
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