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

HRID 1875342Notes

Reaction equation

HRID 1875342 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

5

Reactant 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 8007ButylamineHCID 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.

Workup

  1. temperatureAfter two hours the mixture is cooled
  2. customthe precipitate formed
  3. filtrationfiltered
  4. washwashed with copious amounts of water

Sources & evidence

ORD record
ord-15cbc30eed7840f59731c28708170544
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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