p-Toluenesulfonic acid → 2,3-Dihydroperimidine

HRID 274155

Reaktionsgleichung

Reaktionsgleichung von HRID 274155
C[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.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.CCOCC>[NH:2]1[C:3]2=[C:12]3[C:7](=[CH:6][CH:5]=[CH:4]2)[CH:8]=[CH:9][CH:10]=[C:11]3[NH:13][CH2:14]1

Komponenten

5

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 140748N,N'-Dimethyl-1,8-naphthalenediamine

Produkt 1

HCID 124409652,3-DihydroperimidineAusbeute 170,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The above aldehyde (1.47 g, 4 mmol) was treated with N,N'-dimethyl-1,8-diaminonaphthalene (4.2 mmol), and para-toluenesulfonic acid (5 mg) in tetrahydrofuran (15 mL) for 20 min at room temperature. The solution was diluted with ether, washed with dilute sodium carbonate, and concentrated. The residue was recrystallized from hexane-ethyl acetate to give the 2,3-dihydroperimidine 7 (1.22 g, 59%): mp 89-90° C.; NMR 7.5-6.75(m, 12H), 6.34(d, 2H), 4.24(t, 1H), 3.9(2t, 4H), 3.02(s, 6H), 1.8-1.2(m, 16H), 0.85(t, 3H).

Aufarbeitung

  1. washwashed with dilute sodium carbonate
  2. concentrationconcentrated
  3. customThe residue was recrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fe932fcba30047168c5dd8664105fc6e
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389285

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