p-Toluenesulfonic acid → 2,3-Dihydroperimidine

HRID 274153

Reaktionsgleichung

Reaktionsgleichung von HRID 274153
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:12])[CH:5]=[CH:4][CH:3]=1.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[NH:1]1[C:2]2=[C:11]3[C:6](=[CH:5][CH:4]=[CH:3]2)[CH:7]=[CH:8][CH:9]=[C:10]3[NH:12][CH2:13]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 680671,8-Diaminonaphthalene

Produkt 1

HCID 124409652,3-DihydroperimidineAusbeute 15.175,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the above aldehyde (1.17 g, 4 mmol), distilled 1,8-diamino naphthalene (0.63 g, 4 mmol), p-toluenesulfonic acid (10 mg), and tetrahydrofuran (6 mL) was stirred for 0.5 h at room temperature. The mixture was basified with 1 mL saturated sodium carbonate, diluted with THF-ether (1:1) and washed with water. The extract was concentrated and the residual solid was recrystallized from THF-ether (1:1, 30 mL) to give the 2,3-dihydroperimidine (1.50 g, 87%): mp 165-167° C.; 1H NMR (CDCl3) 7.59(s, 4H), 7.45 and 6.9(2d, 4H), 7.1(m, 4H), 6.4(d, 2H), 4.7(bs, 2H), 4.45(t, 1H), 4.0(t, 2H), 2.0-1.5(m, 8H); IR 3385, 3360, 2225, 1601 cm-1.

Aufarbeitung

  1. washwashed with water
  2. concentrationThe extract was concentrated
  3. customthe residual solid was recrystallized from THF-ether (1:1, 30 mL)

Quellen und Nachweise

ORD-Eintrag
ord-e70ac4add3514d1bbc9b8c0076e1cb7c
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389285

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