Hydrochloric Acid → (+/-)-alpha-(3,4-Dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrile

HRID 351562

Reaktionsgleichung

Reaktionsgleichung von HRID 351562
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].CO[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=1[CH3:26].Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:16]2[C:17]([CH3:26])=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][C:21]=2[CH3:22])[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 1398352-Methoxy-1,3-dimethyl-5-nitrobenzene

Produkt 1

HCID 22312926(+/-)-alpha-(3,4-Dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of (3,4-dichlorophenyl)acetonitrile (0.149 mol) in DMF (100 ml) was stirred at 0° C. under N2 flow. Sodium hydride (0.223 mol) was added portionwise. The mixture was stirred at 0° C. under N2 flow for 1 hour. A mixture of, 2-methoxy-1,3-dimethyl-5-nitrobenzene (0.149 mol) in DMF (100 ml) was added dropwise at 0° C. under N2 flow. The mixture was stirred at RT for 6 hours, then cooled, hydrolized with H2O and with HCl 3N and extracted with EtOAc. The organic layer was separated, washed several times with H2O, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 43.4 g (87%) of (±)-α-(3,4-dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrile (interm. 48).

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. under N2 flow for 1 hour
  2. additionwas added dropwise at 0° C. under N2 flow
  3. stirringThe mixture was stirred at RT for 6 hours
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed several times with H2O
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was crystallized from DIPE
  11. filtrationThe precipitate was filtered off
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e22c4e17d82f4d52a1b42abd2bf3c54c
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743792B2

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