3-(Dimethylamino)-2-propenal → HCID 178467801, compound

HRID 406520

Reaction equation

HRID 406520 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[NH+]1C=CC=CC=1.[CH3:12][N:13]([CH3:19])/[CH:14]=[CH:15]/[C:16](=[O:18])[CH3:17].[CH3:20][N:21]([CH3:26])[CH:22]=[CH:23][CH:24]=O>C(OC(=O)C)(=O)C.C(O)(=O)C>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:12][N:13]([CH3:19])[CH:14]=[C:15]([C:16](=[O:18])[CH3:17])[CH:24]=[CH:23][CH:22]=[N+:21]([CH3:26])[CH3:20]

Participants

5

Reactant 3

HCID 791253-(Dimethylamino)-2-propenalHCID 5369152trans-4-(Dimethylamino)-3-buten-2-oneHCID 11019233Borate(1-), tetrafluoro-, hydrogen, compd. with pyridine (1:1:1)

Product 1

HCID 178467801HCID 178467801, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21895370AcOH AcOAcSolvent

Conditions

Temperature
0 °C

Procedure

Pyridinium tetrafluoroborate (2.21 g, 13.3 mmol) was added to a solution of (3E)-4-(dimethylamino)-3-buten-2-one (1.54 ml, 13.3 mmol) in 13.5 ml acetic anhydride/acetic acid (2:1). The resulting suspension was cooled to 0° C. and 3-dimethylaminoacroleine (1.33 ml, 13.3 mmol) was added over a period of 1 h under vigorous stirring and cooling with an ice bath receiving a red-brown precipitate. The cool reaction mixture was filtered and the remaining solid was washed with diethylether several times and dried under reduced pressure. The pentamethinium salt was obtained as orange crude product (2.69 g, 96%) and was used without any further purification.

Workup

  1. temperaturecooling with an ice bath
  2. customThe cool reaction mixture
  3. filtrationwas filtered
  4. washthe remaining solid was washed with diethylether several times
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd552ca6e27549e988c610e8cce96ebb
Source dataset
uspto-grants-2014_06
Patent number
US08754111B2

Linked notes

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