Triethylamine → HCID 86741123, compound

HRID 1731993Notes

Reaction equation

HRID 1731993 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][C@H:5]2[C@@H: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 86741123HCID 86741123, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.06 gm (6.38 nmole) of decalin-1,3-dione in 3 mL of dry ethanol was cooled in an ice bath and treated with 0.89 mL of (6.4 mmole) triethylamine followed by 1.128 gm (6.50 mmole) of p-toluenesulfonyl azide. The mixture was stirred in the ice bath for 4 hours, then concentrated in vacuo (less than 40° C.). The residue was dissolved in 45 mL of ether and the ether washed with a solution of 0.42 gm KOH in 30 mL of water, dried (Na2SO4), filtered, and concentrated to 1.22 gm of an orange oil. This was chromatographed on 40-micron silica giving 0.45 gm of trans-2-diazodecalin-1,3-dione, mp 81°-3° C.

Workup

  1. concentrationconcentrated in vacuo (less than 40° C.)
  2. dissolutionThe residue was dissolved in 45 mL of ether
  3. washthe ether washed with a solution of 0.42 gm KOH in 30 mL of water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to 1.22 gm of an orange oil
  7. customThis was chromatographed on 40-micron silica giving 0.45 gm of trans-2-diazodecalin-1,3-dione, mp 81°-3° C.

Sources & evidence

ORD record
ord-0c22d4064dea420f8342e19d1f1a3d5a
Source dataset
uspto-grants-1986_11
Patent number
US04624908

Reaction notes

Loading…