Sulfuric Acid → HCID 69551232, compound

HRID 1822760Notes

Reaction equation

HRID 1822760 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 69551232HCID 69551232, compound

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-9aac5d6e5c9949759aaa4c43a2c00783
Source dataset
uspto-grants-2006_05
Patent number
US07037924B2

Reaction notes

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