2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 69235551, compound

HRID 1611479Notes

Reaction equation

HRID 1611479 reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[C:9]([NH2:12])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH:16]=[C:17]([C:23]#[N:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>C1(C)C=CC=CC=1>[C:23]([C:17](=[CH:16][NH:12][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:11][CH:10]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:24]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 155262915-Phenylthiophen-3-amine

Product 1

HCID 69235551HCID 69235551, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-phenyl-3-thienylamine (1.00 g, 5.7 mmol) and ethyl (ethoxymethylene)cyanoacetate (950 mg, 5.7 mmol) in 20 mL of toluene is heated at reflux for 45 minutes. The reaction mixture is filtered while warm and the collected solid is washed with diethyl ether to provide 198 mg of ethyl 2-cyano-3-[(5-phenyl-3-thienyl)amino]-2-propenoate as white crystals, mp 190-193° C.; MS 296.9 (M−H)−.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 45 minutes
  3. filtrationThe reaction mixture is filtered
  4. temperaturewhile warm
  5. washthe collected solid is washed with diethyl ether

Sources & evidence

ORD record
ord-179c063f038e48bfa1c37844fc2ac404
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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