Butanal → 2,3-Dihydro-1,3-dimethyl-2-propyl perimidine

HRID 2372015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2372015
[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][CH3:14])[CH:6]=[CH:5][CH:4]=1.[CH:15](=O)[CH2:16][CH2:17]C.[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>O.O1CCCC1>[CH3:14][N:13]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[N:2]([CH3:20])[CH:1]1[CH2:15][CH2:16][CH3:17]

Komponenten

7

Edukt 4

HCID 261ButanalHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 140748N,N'-Dimethyl-1,8-naphthalenediamine

Produkt 1

HCID 199057282,3-Dihydro-1,3-dimethyl-2-propyl perimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of N,N'-dimethyl-1,8-naphthalene diamine (prepared in Example 1) (0.93 g, 5 mmol), distilled butyraldehyde (0.43 g, 6 mmol), p-toluene sulfonic acid (5 mg), and tetrahydrofuran (5 ml), was stirred at room temperature for 15 minutes. The mixture was basified with 25% sodium hydroxide (1.0 ml), diluted with water (20 ml) and extracted with ethyl ether (100 ml). The extract was dried over potassium carbonate and concentrated to an oil which was recrystallized from ether-hexane to give crystals of 2,3-dihydro-1,3-dimethyl-2-propyl perimidine: mp 70°-71° C.; NMR (CDCl3) 7.08(m, 4H), 6.29(m, 2H), 4.22(t, 1H), 3.03(s, 6H), 1.4(m, 4H), 0.8(t, 3H); IR (KBr) 1592, 1582 cm-1.

Aufarbeitung

  1. extractionextracted with ethyl ether (100 ml)
  2. dry with materialThe extract was dried over potassium carbonate
  3. concentrationconcentrated to an oil which
  4. customwas recrystallized from ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0ac0b20b73da4f768285e83a2a21e0a9
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05097029

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