Acetic Acid → 3-(2-Nitroethenyl)thiophene
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureAfter 60 minutes of refluxing
- temperaturethe mixture was cooled
- customthe solid was collected
- 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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