Sodium Chloride → 2-Cyano-3-(benzothiophen-7-yl)-acrylic acid methyl ester

HRID 974376Notes

Reaction equation

HRID 974376 reaction equation
[S:1]1[C:5]2[C:6]([CH:10]=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH3:12][O:13][C:14](=[O:18])[CH2:15][C:16]#[N:17].C([O-])(=O)C.[NH4+].[Na+].[Cl-]>C(OCC)(=O)C.C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:12][O:13][C:14](=[O:18])[C:15]([C:16]#[N:17])=[CH:10][C:6]1[C:5]2[S:1][CH:2]=[CH:3][C:4]=2[CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 7747Methyl cyanoacetateHCID 517165Ammonium AcetateHCID 107021381-Benzothiophene-7-carbaldehyde

Product 1

HCID 542064742-Cyano-3-(benzothiophen-7-yl)-acrylic acid methyl esterYield 99.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.0 g (6.2 mmoles) of 7-benzothiophene-carbaldehyde, 0.4 g (6.8 mmoles) of cyanoacetic acid methyl ester, 0.07 g of ammonium acetate, 0.2 g of acetic acid, 1 g of molecular sieve (3 Å) and 10 ml of toluene are boiled under reflux for 4 hours, and then the reaction mixture is cooled and mixed with 20 ml of ethyl acetate and with 20 ml of 10% NaCl solution. The separated organic phase is dried with MgSO4, filtered and the solvent is evaporated in vacuo. 1.5 g of 2-cyano-3-(benzothiophen-7-yl)-acrylic acid methyl ester in the form of a crude product is obtained as residue.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturethe reaction mixture is cooled
  3. dry with materialThe separated organic phase is dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-d20bf3cb467d4a3db414f6336c89fb2f
Source dataset
uspto-grants-1991_11
Patent number
US05068359

Reaction notes

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