Water → HCID 20153684, compound

HRID 2414046Notes

Reaction equation

HRID 2414046 reaction equation
[Se](=O)=O.O.[CH2:5]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH3:21])=[CH:16][CH:15]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:23]/[C:24](/[C:29]#[N:30])=[C:25](\[NH2:28])/[C:26]#[N:27]>O1CCOCC1.C(O)(=O)C>[CH2:5]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:23]=[C:24]([C:29]#[N:30])[C:25]([C:26]#[N:27])=[N:28][CH:21]=2)=[CH:16][CH:15]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 24007Selenium DioxideHCID 2723951DiaminomaleonitrileHCID 2724918HCID 2724918, compound

Product 1

HCID 20153684HCID 20153684, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Selenium dioxide in an amount of 11.4 g (0.1 mol) was mixed with 100 ml of dioxide and 2 ml of water. The mixture was stirred for 2 hours at 70°-75° C., and a solution of 24.8 g (0.1 mol) of p-octyloxyacetophenone in 60 ml of dioxane was added thereto. After 2 hours of refluxing, the mixture was cooled to precipitate metal selenium, which was then removed by filtration. Into the filtrate were added 10.8 g (0.1 mol) of diaminomaleonitrile and 3.0 ml of acetic acid, and the mixture was refluxed for 2 hours at 90°-93° C. After the reaction, the mixture was subjected to cooling and filtration, and the filtrate was condensed to obtain a crude product. The crude product was subjected to recrystallization from hexane to obtain 27.2 g (82% yield) of the product. The meling point: 79° C., IR (νcm-1): 2245 (C≡N).

Workup

  1. temperatureAfter 2 hours of refluxing
  2. temperaturethe mixture was cooled
  3. customto precipitate metal selenium, which
  4. customwas then removed by filtration
  5. temperaturethe mixture was refluxed for 2 hours at 90°-93° C
  6. customAfter the reaction
  7. temperatureto cooling
  8. filtrationfiltration
  9. customcondensed
  10. customto obtain a crude product
  11. customThe crude product was subjected to recrystallization from hexane

Sources & evidence

ORD record
ord-776364602b7b4b75a081254107dd0b26
Source dataset
uspto-grants-1988_01
Patent number
US04721367

Reaction notes

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