1,8-Diaminonaphthalene → 2,3-Dihydroperimidine

HRID 1768899

Reaktionsgleichung

Reaktionsgleichung von HRID 1768899
[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.Cl[CH2:14]CCC(C1C=CC=CC=1)=O>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[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][CH2:14]1

Komponenten

5

Edukt 2

HCID 680671,8-DiaminonaphthaleneHCID 2535334-Chlorobutyrophenone

Produkt 1

HCID 124409652,3-DihydroperimidineAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred mixture of 1.411 g of 1,8-diaminonaphthalene, 1.629 g of 4-chlorobutyro-phenone, 3 mg of p-toluenesulfonic acid monohydrate, and 10 mL of toluene was heated to reflux under a nitrogen atmosphere using a Dean-Stark trap to remove the water evolved from the reaction for 10 hr. The mixture was filtered to remove unreacted starting material, partioned between ethyl acetate and 5% sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 2.04 g of crude product. This was further purified by chromatography on silica gel, eluting with 1:1 diethyl ether/petroleum ether, and collecting the initial band to yield 0.719 g of dihydroperimidine intermediate.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under a nitrogen atmosphere
  3. customto remove the water
  4. customevolved from the reaction for 10 hr
  5. filtrationThe mixture was filtered
  6. customto remove unreacted
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give 2.04 g of crude product
  11. customThis was further purified by chromatography on silica gel
  12. washeluting with 1:1 diethyl ether/petroleum ether
  13. customcollecting the initial band

Quellen und Nachweise

ORD-Eintrag
ord-0afe8927cbfd4921aeee83560246b418
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380635

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