Acetic Acid → 2-(2-Nitro-1-propen-1-yl)thiophene

Reaction equation

C([C:3]1[CH:7]=[CH:6][S:5][CH:4]=1)=O.[N+:8]([CH2:11][CH3:12])([O-:10])=[O:9].[CH2:13](N)CCC.C(O)(=O)C>>[N+:8]([C:11]([CH3:13])=[CH:12][C:6]1[S:5][CH:4]=[CH:3][CH:7]=1)([O-:10])=[O:9]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 6587Nitroethane

HCID 8007Butylamine

HCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 2382342-(2-Nitro-1-propen-1-yl)thiophene

Conditions

Temperature: 80 °C

Procedure

5.0 g (44.6 mmol) 3-formylthiophene are dissolved together with 8.9 ml (124.8 mmol) nitroethane, 5.3 ml (53.5 mmol) butylamine in 25.1 ml glacial acetic acid (454.7 mmol) and heated to 80° C. After two hours the mixture is cooled and the precipitate formed is suction filtered and washed with copious amounts of water. The crude product thus obtained is dissolved in ethyl acetate, dried on sodium sulphate and evaporated down i. vac.