Water → 3-Anilino-2-(4-methoxy--naphthylmethyl)acrylonitrile

HRID 746206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 746206
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=O)=[CH:5][CH:4]=1.[NH:15]([CH2:22][CH2:23][C:24]#[N:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[O-].[Na+].O>CS(C)=O.CO.C(O)C>[NH:15]([CH:22]=[C:23]([CH2:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:24]#[N:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 141003-AnilinopropionitrileHCID 852174-Methoxy-1-naphthaldehydeHCID 10942334Sodium Methoxide

Produkt 1

HCID 704518803-Anilino-2-(4-methoxy--naphthylmethyl)acrylonitrileAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 4-methoxy-1-naphthaldehyde (10.0 g, 53.7 mmol)and 3-anilinopropionitrile (9.0 g, 61.6 mmol) in dimethylsulfoxide (25 mL) was added a solution of sodium methoxide (2.9 g, 53.6 mmol) in methanol (25 mL). The resulting mixture was heated to 133° with distillation of the methanol over 45 min. The reaction was then cooled, diluted with ethanol:water and the precipitate that formed was collected, washed with water, ethanol and hexane to give the title compound (10.28 g, 61%); mp 188°-189° after recrystallization from 2-methoxyethanol. Anal. Calcd for C21H18N2O: C, 80.23; H, 5.77; N, 8.91. Found: C, 79.80; H, 5.74; N, 8.87.

Aufarbeitung

  1. temperatureThe reaction was then cooled
  2. customwas collected
  3. washwashed with water, ethanol and hexane

Quellen und Nachweise

ORD-Eintrag
ord-78ab4148ab2c4228ad0fc9acb2867a4b
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04603136

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