Triethylamine → 2-Diazodecalin-1,3-dione

HRID 46787

Reaction equation

HRID 46787 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 125563532-Diazodecalin-1,3-dioneYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4f525636ee6d46309ff284fbd1d279c0
Source dataset
uspto-grants-1979_11
Patent number
US04175135

Linked notes

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