Dimethyl acetylenedicarboxylate → Dimethyl 3-thienylaminobutenedioate

HRID 365074Notes

Reaction equation

HRID 365074 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH3:7][O:8][C:9]([C:11]#[C:12][C:13]([O:15][CH3:16])=[O:14])=[O:10]>CO>[S:4]1[CH:5]=[CH:6][C:2]([NH:1][C:11](=[CH:12][C:13]([O:15][CH3:16])=[O:14])[C:9]([O:8][CH3:7])=[O:10])=[CH:3]1

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 640543Thiophen-3-amine

Product 1

HCID 56624739Dimethyl 3-thienylaminobutenedioate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Aminothiophene is redissolved in methanol (500 mL) cooled in an ice bath and dimethylacetylenedicarboxylate (80 g; 0.50 mol) is added dropwise. The mixture is stirred at room temperature for 15 hours and 30 minutes, the methanol removed under reduced pressure and 1,2-dichloroethane is added. This solvent is also evaporated off to give dimethyl 3-thienylaminobutenedioate as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. customthe methanol removed under reduced pressure and 1,2-dichloroethane
  3. additionis added
  4. customThis solvent is also evaporated off

Sources & evidence

ORD record
ord-d032adb4cc5c46af9c30c28a3ad717af
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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