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

HRID 1833237Notes

Reaction equation

HRID 1833237 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].[C:16](=[O:21])([O:18][CH2:19][CH3:20])[NH2:17].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:21])[NH:17][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)[CH3:20]

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 esterYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
1110 °C

Procedure

To a stirred solution of 2-(3,4-dimethoxy-phenyl)-3-oxo-propionitrile (26 g, 127 mmol) in toluene ((275 mL) was added ethyl carbamate (11.3 g, 127 mmol) and concentrated sulfuric acid solution (2.0 mL). The reaction mixture was heated at 1110° C. with a Dean-Stark apparatus. The mixture was cooled and a solid was precipitated. The mixture was filtered and the solid was collected. The yellow solid was washed with diethyl ether to afford [2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-carbamic acid ethyl ester (20 g, 57% yield).

Workup

  1. temperatureThe mixture was cooled
  2. customa solid was precipitated
  3. filtrationThe mixture was filtered
  4. customthe solid was collected
  5. washThe yellow solid was washed with diethyl ether

Sources & evidence

ORD record
ord-35b4b74389e74bed8d2a85ab763df12a
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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