Selenium Dioxide → HCID 21291309, compound

HRID 622651Notes

Reaction equation

HRID 622651 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:5]2[CH:6]=[CH:7][C:8]3[C:9]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:10]C(C)=[N:12][C:13]=3[C:14]=2[N:15]=1.[Se](=O)=[O:30].[O:32]1[CH2:37][CH2:36]OCC1>O>[C:17]1([C:9]2[C:8]3[C:13](=[C:14]4[C:5](=[CH:6][CH:7]=3)[C:4]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:3][C:2]([CH:1]=[O:30])=[N:15]4)[N:12]=[C:36]([CH:37]=[O:32])[CH:10]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 651491,10-Phenanthroline, 2,9-dimethyl-4,7-diphenyl-

Product 1

HCID 21291309HCID 21291309, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of bathocuproine (0.8 g, 2.2 mmole), selenium dioxide (1.16 g, 10.4 mmole), dioxane (29.6 ml) and water (1.25 ml) was heated with stirring in an oil bath at 110° for 2 hr. The hot mixture was then filtered through Celite to remove selenium metal. Water was added to the hot filtrate until slight cloudiness appeared. The mixture was then placed in the refrigerator to allow the product to precipitate. The product, which was contaminated by red selenium metal, was collected by vacuum filtration. Yield=88%. Mp=165°-170°. IR 3200-3600, 2800-3050, 1717, 1590, 1550, 1495, 1445, 1400, 1355, 1295, 1255, 1190, 1120, 1080, 875, 780, 705, 620 cm-1. 60 MHz proton NMR in CDCl3 δ7.2 (10 protons), δ7.7, δ7.95 (4 protons), δ10.05 (<2 protons).

Workup

  1. temperaturewas heated
  2. filtrationThe hot mixture was then filtered through Celite
  3. customto remove selenium metal
  4. additionWater was added to the hot filtrate until slight cloudiness
  5. customto precipitate
  6. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-4aaecf5649f84194af83aa268649f14f
Source dataset
uspto-grants-1988_09
Patent number
US04772563

Reaction notes

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