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 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
- temperatureAfter a 60 min reflux period
- temperaturethe mixture was cooled
- customthe solid was collected
- 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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