Nitric Acid → HCID 135556898, compound

HRID 1288434Notes

Reaction equation

HRID 1288434 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][N:7]1[CH2:16][C:15](=[O:17])[NH:14][C:8]1=[N:9]2.[N+:18]([O-])([OH:20])=[O:19].[N+]([O-])(O)=O.S(=O)(=O)(O)O>C(#N)C>[N+:18]([C:13]1[C:4]([CH2:3][O:2][CH3:1])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]1[NH:14][C:15](=[O:17])[CH2:16][N:7]1[CH2:6]2)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 71777668Sulfuric acid, mixt. with nitric acidHCID 1355568956-(Methoxymethyl)-5,10-dihydroimidazo[2,1-b]quinazolin-2(3H)-one

Product 1

HCID 135556898HCID 135556898, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred, 0° suspension of 11.20 g. (6.0 × 10-2 moles) of 6-methoxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]-quinazolin-2-one in acetonitrile (150 ml.) is added dropwise 83.0 g. (6.6 × 1012 moles of nitric acid) of a 5% nitric acid/sulfuric acid solution. The mixture is allowed to stir at 0° for 45 minutes, warmed to room temperature and stirred an additional two hours. The mixture is poured into 700 ml. of ice water, the organic layer separated, the acidic aqueous solution washed with methylene chloride (2 × 100 ml.) and filtered. The aqueous solution is made basic (pH 8) by the dropwise addition of 40% sodium hydroxide, the basic solution stirred for 30 minutes and the precipitate filtered under suction. The yellow solid is washed with water, then acetone and dried under high vacuum. The solid is suspended in water (350 ml.), the solution saturated with hydrogen chloride, heated to boiling and filtered. Saturated sodium chloride solution (100 ml.) is added, the mixture cooled and the precipitate isolated yielding the title product as a yellow powder.

Workup

  1. additionTo a stirred, 0° suspension of 11.20 g
  2. stirringstirred an additional two hours
  3. additionThe mixture is poured into 700 ml
  4. customof ice water, the organic layer separated
  5. washthe acidic aqueous solution washed with methylene chloride (2 × 100 ml.)
  6. filtrationfiltered
  7. additionby the dropwise addition of 40% sodium hydroxide
  8. stirringthe basic solution stirred for 30 minutes
  9. filtrationthe precipitate filtered under suction
  10. washThe yellow solid is washed with water
  11. dry with materialacetone and dried under high vacuum
  12. temperaturethe solution saturated with hydrogen chloride, heated
  13. filtrationfiltered
  14. additionSaturated sodium chloride solution (100 ml.) is added
  15. temperaturethe mixture cooled
  16. customthe precipitate isolated

Sources & evidence

ORD record
ord-beda128720d14d03b90d45b417344072
Source dataset
uspto-grants-1976_10
Patent number
US03988340

Reaction notes

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