3-(Dimethylamino)-2-propenal → HCID 178500406, compound

HRID 2040735

Reaction equation

HRID 2040735 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[NH+:6]1[CH:11]=[CH:10][CH:9]=C[CH:7]=1.[CH3:12][N:13]([CH3:18])[CH:14]=[CH:15][CH:16]=[O:17].[C:19](OC(=O)C)(=[O:21])C.[C:26](O)(=O)C>>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:12][N:13]([CH3:18])[CH:14]=[C:15]([C:16]([O:21][CH3:19])=[O:17])[CH:9]=[CH:10][CH:11]=[N+:6]([CH3:26])[CH3:7]

Participants

4

Reactant 3

HCID 791253-(Dimethylamino)-2-propenalHCID 11019233Borate(1-), tetrafluoro-, hydrogen, compd. with pyridine (1:1:1)HCID 21895370AcOH AcOAc

Product 1

HCID 178500406HCID 178500406, compoundYield 65%

Conditions

Temperature
0 °C

Procedure

Pyridiniumtetrafluoroborate (283.7 g, 1.70 mol) was added to a solution of methyl-(2E)-3-(3-dimethylamino)prop-2-enoate in 442.5 ml acetic anhydride/acetic acid (2:1). The resulting suspension was cooled to 0° C. and 3-dimethylaminoacroleine (169.9 ml, 1.70 mol) was added slowly over the course of 3 hrs. under vigorous stirring and cooling with an ice bath, a yellow-brown precipitate formed. After further stirring for 2 hrs. at room temperature the reaction mixture was filtered. The remaining solid was washed with diethylether several times and dried under reduced pressure. Re crystallization from i-propanol/ethanol (2:1) gave 326.7 g (65%) of the pentamethinium salt as yellow crystals.

Workup

  1. temperaturecooling with an ice bath
  2. customa yellow-brown precipitate formed
  3. stirringAfter further stirring for 2 hrs
  4. filtrationat room temperature the reaction mixture was filtered
  5. washThe remaining solid was washed with diethylether several times
  6. customdried under reduced pressure
  7. customRe crystallization from i-propanol/ethanol (2:1)

Sources & evidence

ORD record
ord-a5d6e144d551412a9f4896dbda643d07
Source dataset
uspto-grants-2013_11
Patent number
US08580949B2

Linked notes

Loading…