Water → 1-Naphthanilide

HRID 905515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 905515
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[NH4+]>C(#N)C.C(OCC)C>[C:15]1([NH:14][C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[O:12])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6115AnilineHCID 14923Ammonium HydroxideHCID 701461-Naphthalenecarbonyl chloride

Produkt 1

HCID 3471821-NaphthanilideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

4.77 g of 1-naphthoyl chloride (TCI America) was dissolved in 100 ml of anhydrous acetonitrile. To the solution so formed, 2.28 ml of aniline (Sigma-Aldrich) was added in a dropwise fashion over a period of c.a. 20 min. The reaction was then refluxed for 2 h at 82° C. 100 ml of distilled water and 5 ml of concentrated ammonium hydroxide were added along with 100 ml of diethyl ether in a separatory funnel. The phases were separated and the aqueous phase was washed with 100 ml of dichloromethane. The organic fractions were collected and dried with magnesium sulfate, filtered and the solvent was then removed under reduced pressure to yield a white solid 5.07 g (82%; 20.5 mmol).

Aufarbeitung

  1. customTo the solution so formed
  2. custom20 min
  3. customThe phases were separated
  4. washthe aqueous phase was washed with 100 ml of dichloromethane
  5. customThe organic fractions were collected
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was then removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cb5847bc2b8849bfbcea377930f23d20
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012458B2

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