Ethyl Acetate → HCID 68821977, compound

HRID 1817208Notes

Reaction equation

HRID 1817208 reaction equation
[S:1]1(=[O:12])(=[O:11])[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:13]([C:15](=[CH:21]OCC)[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14].C(OCC)(=O)C>C(O)C>[C:13]([C:15](=[CH:21][NH:10][C:8]1[CH:7]=[CH:6][C:5]2[S:1](=[O:11])(=[O:12])[CH2:2][CH2:3][C:4]=2[CH:9]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 441222605-Amino-2,3-dihydro-1H-1-benzothiophene-1,1-dione

Product 1

HCID 68821977HCID 68821977, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g (27.3 mmol) of 2,3-dihydro-1-benzothiophen-5-amine 1,1-dioxide were suspended in 50 ml of ethanol under argon, 4.62 g (1 eq, 27.3 mmol) of ethyl 2-cyano-3-ethoxyacrylate were added, and the mixture was heated under reflux overnight. For working up, ethyl acetate was added to the mixture, and the precipitate which formed was filtered off with suction on a frit. The solid was dried in vacuo at 50° C. for 1.5 h. 6.87 g (81%) of the target compound were isolated and were employed without further purification in the next stage.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customthe precipitate which formed
  4. filtrationwas filtered off with suction on a frit
  5. customThe solid was dried in vacuo at 50° C. for 1.5 h

Sources & evidence

ORD record
ord-1df3be3e4d1b425eabb065482162a092
Source dataset
uspto-grants-2009_10
Patent number
US07598263B2

Reaction notes

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