Triethylamine → 2-Diazodecalin-1,3-dione

HRID 46787

Reaktionsgleichung

Reaktionsgleichung von HRID 46787
[C:1]1(=[O:12])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][C:3](=[O:11])[CH2:2]1.C(N(CC)CC)C.C1(C)C=CC(S([N:29]=[N+:30]=[N-])(=O)=O)=CC=1>C(O)C>[N+:29](=[C:2]1[C:3](=[O:11])[CH2:4][CH:5]2[CH:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)[C:1]1=[O:12])=[N-:30]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 12453943Hexahydronaphthalene-1,3(2h,4h)-dione

Produkt 1

HCID 125563532-Diazodecalin-1,3-dioneAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A solution of 10.0 g (0.0768 mol) of decalin-1,3-dione in 50 ml of ethanol was magnetically stirred under nitrogen and cooled to -10° C. To the solution was added 7.77 g (0.0768 mol) of triethylamine followed by 15.14 g (0.0768 mol) of p-toluenesulfonylazide added all at once. The mixture was stirred for one hour at 0° C., and the solvent removed at reduced pressure at a temperature of less than 40° C. To the residue was added 200 ml of ether, and the ether removed to yield a yellow solid. This was recrystallized from ethanol to give 5.23 g of yellow crystals, mp 81°-83° C.

Aufarbeitung

  1. additionadded all at once
  2. customthe solvent removed at reduced pressure at a temperature of less than 40° C
  3. additionTo the residue was added 200 ml of ether
  4. customthe ether removed
  5. customto yield a yellow solid
  6. customThis was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4f525636ee6d46309ff284fbd1d279c0
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175135

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