Water → HCID 131723092, compound

HRID 1250270Notes

Reaction equation

HRID 1250270 reaction equation
[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:9]=1)[CH3:4].[O:19]=[C:20]([OH:32])[C@@H:21]([C@H:23]([C@H:25]([C@@H:27]([C:29]([OH:31])=[O:30])[OH:28])[OH:26])[OH:24])[OH:22].O>C(O)C>[O:19]=[C:20]([OH:32])[C@@H:21]([C@H:23]([C@H:25]([C@@H:27]([C:29]([OH:31])=[O:30])[OH:28])[OH:26])[OH:24])[OH:22].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:9]=1)[CH3:4].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10198785HCID 10198785, compound

Product 1

HCID 131723092HCID 131723092, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a hot solution of (4E)-N-methyl-5-(3-acetamido-4-methylphenyl)-4-penten-2-amine (600 mg, 2.43 mmol) in ethanol (40 mL) was added galactaric acid (256 mg, 2.20 mmol). The mixture was heated to reflux and water (0.5 mL) was added drop-wise. The clear solution was filtered to remove some insoluble particles. The filtrate was concentrated to 25 mL and cooled to ambient temperature. The precipitate was filtered, washed with anhydrous ether and dried in a vacuum oven at 45° C. for 16 h to yield 712 mg (83.3%) of a white powder, mp 160-163° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationThe clear solution was filtered
  4. customto remove some insoluble particles
  5. concentrationThe filtrate was concentrated to 25 mL
  6. filtrationThe precipitate was filtered
  7. washwashed with anhydrous ether
  8. customdried in a vacuum oven at 45° C. for 16 h

Sources & evidence

ORD record
ord-80c71cb6af7047d88f6a72df374029fb
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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