Acetic Acid → 3-(2-Nitrovinyl)thiophene

HRID 487313Notes

Reaction equation

HRID 487313 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[N+:8]([CH3:11])([O-:10])=[O:9].C(N)C1C=CC=CC=1.C(O)(=O)C>CC(O)C>[N+:8]([CH:11]=[CH:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 7504BenzylamineHCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 27324183-(2-Nitrovinyl)thiopheneYield 56%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

When R2Was H the thiophene-3-carboxaldehyde (1 eq) was dissolved in 2-propanol and treated with nitromethane (1 eq), benzylamine (0.065 eq) and glacial acetic acid (0.1 3 eq). After a 60 min reflux period, the mixture was cooled and the solid was collected and washed with ice-cold ether to afford the product (56%); mp 94.5°-96.5° C.

Workup

  1. temperatureAfter a 60 min reflux period
  2. temperaturethe mixture was cooled
  3. customthe solid was collected
  4. washwashed with ice-cold ether

Sources & evidence

ORD record
ord-49a3023ea9524861ac2ae27c7d3f4367
Source dataset
uspto-grants-1994_03
Patent number
US05294621

Reaction notes

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