Potassium Hydroxide → 3-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-2,4-(1H,3H)quinazolinedione

HRID 1973445Notes

Reaction equation

HRID 1973445 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.O[CH2:13][CH2:14][N:15]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=[C:16]1[CH3:23].[NH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=[O:34])[NH:26][C:25]1=[O:35].[OH-].[K+]>CN(C)C=O.CO.C1(C)C=CC=CC=1>[CH3:23][C:16]1[N:15]([CH2:14][CH2:13][N:26]2[C:27](=[O:34])[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:24][C:25]2=[O:35])[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 64048QuinazolinedioneHCID 867342581-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole tosylate

Product 1

HCID 214916603-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-2,4-(1H,3H)quinazolinedione

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 15.0 parts of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole tosylate and 7.5 parts of 2,4(1H,-3H)-quinazolinedione is dissolved in 190 parts of warm dimethylformamide. 2.9 Parts of potassium hydroxide is dissolved in 80 parts of methanol and diluted with about 95 parts of dimethylformamide. The methanol is removed under reduced pressure, the residual solution added to the quinazolinedione solution, and the resulting mixture heated on a steam bath for 4 hours. The crude solution is cooled, filtered, and diluted with 100 parts of water. The precipitate which forms is separated by filtration and the solvent is evaporated from the filtrate to leave a residue which is stirred with 630 parts of toluene and filtered. The solvent is evaporated from the filtrate to leave a yellow residue. This is dissolved in toluene and dimethylformamide and then concentrated. A precipitate forms and it is separated by filtration to give 3-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-2,4-(1H,3H)quinazolinedione melting at about 261°-264° C.

Workup

  1. customThe methanol is removed under reduced pressure
  2. additionthe residual solution added to the quinazolinedione solution
  3. temperaturethe resulting mixture heated on a steam bath for 4 hours
  4. temperatureThe crude solution is cooled
  5. filtrationfiltered
  6. additiondiluted with 100 parts of water
  7. customThe precipitate which forms is separated by filtration
  8. customthe solvent is evaporated from the filtrate
  9. customto leave a residue which
  10. filtrationfiltered
  11. customThe solvent is evaporated from the filtrate
  12. customto leave a yellow residue
  13. concentrationdimethylformamide and then concentrated
  14. customA precipitate forms and it is separated by filtration

Sources & evidence

ORD record
ord-964f7b047905449f9f12c37e2028ac04
Source dataset
uspto-grants-1976_12
Patent number
US03997572

Reaction notes

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