Acetic Acid → 3-(2-Nitrovinyl)thiophene

HRID 1033563Notes

Reaction equation

HRID 1033563 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-0ec95865eb6a47d8b36470c4c605d77d
Source dataset
uspto-grants-1994_05
Patent number
US05310941

Reaction notes

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