Acetic Acid → 3-(2-Nitrovinyl)thiophene

HRID 247899Notes

Reaction equation

HRID 247899 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 R2 is 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 (0.13 eq). After 60 minutes of refluxing, the mixture was cooled, the solid was collected and washed with ice-cold ether to afford the product (56%); mp 94.5°-96.5° C.

Workup

  1. temperatureAfter 60 minutes of refluxing
  2. temperaturethe mixture was cooled
  3. customthe solid was collected
  4. washwashed with ice-cold ether

Sources & evidence

ORD record
ord-197ef4f7558e43b9b14b9295f4e89986
Source dataset
uspto-grants-1993_05
Patent number
US05208252

Reaction notes

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