Ethyl 2-azido-3-(5-methylthiophen-2-yl)acrylate → ethyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 518124Notes

Reaction equation

HRID 518124 reaction equation
[N:1]([C:4](=[CH:10][C:11]1[S:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C=CC=C(C)C=1>[CH3:16][C:13]1[S:12][C:11]2[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1][C:15]=2[CH:14]=1

Participants

3

Reactant 1

HCID 76601917Ethyl 2-azido-3-(5-methylthiophen-2-yl)acrylate

Product 1

HCID 1438928ethyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylateYield 85.9%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

Ethyl 2-azido-3-(5-methylthiophen-2-yl)acrylate (3.38 g) was dissolved in m-xylene (30 mL) and the mixture was heated at reflux for 1 hour. The reaction solution was concentrated under reduced pressure. To the residue was added n-hexane and the residue was washed with n-hexane. The solid was collected by filtration, and dried under reduced pressure to give the title compound (2.56 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionTo the residue was added n-hexane
  5. washthe residue was washed with n-hexane
  6. filtrationThe solid was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-98005136887b4bbd8f6d888542a7406e
Source dataset
uspto-grants-2015_08
Patent number
US09115144B2

Reaction notes

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