Sulfuric Acid → [2-Cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-carbamic acid ethyl ester

HRID 1833255Notes

Reaction equation

HRID 1833255 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH:14]=O)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[NH:16][CH:14]=[C:11]([C:12]#[N:13])[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:21]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5641Carbamic acid, ethyl esterHCID 164773122-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile

Product 1

HCID 69551232[2-Cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the mixture of 2-(3,4-Dimethoxy-phenyl)-3-oxo-propionitrile (20.5 g, 0.1 mol), urethane (8.9 g, 0.1 mol) in toluene (400 mL) was added concentrated sulfuric acid (0.5 mL, 10 mmol). The mixture was refluxed and was concentrated by slow distillation to a volume to about 50 mL. The cooled mixture was filtered and the precipitate was washed with benzene and dried. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 20% methylenechloride) afforded [2-Cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-carbamic acid ethyl ester as a solid: LC-MS m/e calcd for C14H16N2O4 (MH+) 277, found 277. 1H NMR (300 MHz) compatible.

Workup

  1. temperatureThe mixture was refluxed
  2. concentrationwas concentrated by slow distillation to a volume to about 50 mL
  3. filtrationThe cooled mixture was filtered
  4. washthe precipitate was washed with benzene
  5. customdried

Sources & evidence

ORD record
ord-31e8786e849a44b18010c08781b90ef4
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

Loading…