Benzene → Serinol Bisphthalonitrile

HRID 39204

Reaktionsgleichung

Reaktionsgleichung von HRID 39204
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[N+]([C:10]1[CH:17]=[CH:16][CH:15]=[C:12]([C:13]#[N:14])[C:11]=1[C:18]#[N:19])([O-])=O.C([O-])([O-])=O.[K+].[K+].C1C=CC=CC=1>CS(C)=O.CC#N>[C:18](#[N:19])[C:11]1[C:12](=[CH:15][CH:16]=[CH:17][CH:10]=1)[C:13]#[N:14].[C:18](#[N:19])[C:11]1[C:12](=[CH:15][CH:16]=[CH:17][CH:10]=1)[C:13]#[N:14].[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4]

Komponenten

7

Edukt 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 68294SerinolHCID 1626521,2-Benzenedicarbonitrile, 3-nitro-2×

Produkt 1

HCID 86633587Serinol Bisphthalonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of serinol (45.8 mg, 0.50 mmol, 1 equiv.), 3-nitrophthalonitrile (258.1 mg, 1.5 mmol, 2.5 equiv.) and K2CO3 (277.4 mg, 2.0 mmol, 4 equiv.) in 3 mL DMSO was stirred at room temperature and monitored periodically by TLC (9:1 benzene:CH3CN). The reaction mixture changed from orange to brown as the reaction occurred. After 90 h, the reaction mixture was heated to 70° C. TLC analysis showed the gradual disappearance of 3-nitrophthalonitrile over the next 8.5 h. The reaction mixture was partitioned between EtOAc and water, and the two layers were separated. The aqueous layer was extracted with EtOAc. This organic extract was combined with the phase-separated organic layer from the original separation, and then this mixture was washed twice with saturated NaHCO3, twice with water, and once with saturated NaCl. TLC analysis of the crude material showed no ninhydrin positive spot. The crude material was purified by flash chromatography using benzene:CH3CN (95:5) to extract the major UV-active spot.

Aufarbeitung

  1. temperaturethe reaction mixture was heated to 70° C
  2. customover the next 8.5 h
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. customthe two layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. extractionThis organic extract
  7. customwas combined with the phase-separated organic layer from the original separation
  8. washthis mixture was washed twice with saturated NaHCO3, twice with water
  9. customThe crude material was purified by flash chromatography
  10. extractionto extract the major UV-active spot

Quellen und Nachweise

ORD-Eintrag
ord-f97695d5d8364f23a12a894e5a9b6c7f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524891B2

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