Ethanol → (Z)-2-Acetylamino-3-dimethylamino-but-2-enoic acid ethyl ester

Reaction equation

[CH3:1][N:2]([CH3:12])/[C:3](=[C:5]1\[N:6]=[C:7]([CH3:11])[O:8][C:9]\1=[O:10])/[CH3:4].[H-].[Na+].[CH2:15]([OH:17])[CH3:16]>>[CH2:15]([O:17][C:9](=[O:10])/[C:5](/[NH:6][C:7](=[O:8])[CH3:11])=[C:3](/[N:2]([CH3:12])[CH3:1])\[CH3:4])[CH3:16]

Participants

Reactant 3

HCID 702Ethanol

HCID 24758Sodium hydride

HCID 67495069(Z)-4-(1-(Dimethylamino)ethylidene)-2-methyloxazol-5(4H)-one

Product 1

HCID 86595898(Z)-2-Acetylamino-3-dimethylamino-but-2-enoic acid ethyl ester

Procedure

4-[1-Dimethylamino-eth-(Z)-ylidene]-2-methyl-4H-oxazol-5-one (7.4 g, 44.0 mmol) was dissolved in ethanol (50 ml), and sodium hydride (0.10 g, 4.4 mmol) was added at room temperature. The dark solution was refluxed for 1 h. The solvent was evaporated, and the crude product [MS: m/e=215.5 (M+H+)] was used without any further purification for the next step.

Workup

temperatureThe dark solution was refluxed for 1 h
customThe solvent was evaporated
customthe crude product [MS: m/e=215.5 (M+H+)] was used without any further purification for the next step

Sources & evidence

ORD record: ord-81f953fea32e40dc8344c7bdb61e680a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293916B2

Reaction notes

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