Phosphoric Acid → 6-Imidazolyl-2-(3,5-dimethoxy-s-triazin-1-yloxy)-1-[(1-pyrazolyl)-oxycarbonyl]-benzene

HRID 5815Notes

Reaction equation

HRID 5815 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([OH:15])[C:11]=1[C:12]([OH:14])=[O:13].O[N:17]1[CH:21]=[CH:20][CH:19]=[N:18]1.[H-].[Na+].Cl[N:25]1[CH2:30][N:29]([O:31][CH3:32])[CH2:28][N:27]([O:33][CH3:34])[CH2:26]1.P(=O)(O)(O)O>O1CCCC1>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[C:11]([C:12]([O:14][N:17]2[CH:21]=[CH:20][CH:19]=[N:18]2)=[O:13])=[C:10]([O:15][N:25]2[CH2:30][N:29]([O:31][CH3:32])[CH2:28][N:27]([O:33][CH3:34])[CH2:26]2)[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 1004Phosphoric AcidHCID 24758Sodium hydrideHCID 30167331-hydroxy-1H-pyrazoleHCID 190972191-Chloro-3,5-dimethoxy-s-triazineHCID 197940666-Imidazolylsalicylic acid

Product 1

HCID 572503046-Imidazolyl-2-(3,5-dimethoxy-s-triazin-1-yloxy)-1-[(1-pyrazolyl)-oxycarbonyl]-benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.75 g (10.8 mmol) of N,N'-carbonylbisimidazole is added to a solution of 1.88 g (10 mmol) of 6-imidazolylsalicylic acid in 30 ml of tetrahydrofuran. After the mixture has been stirred for 30 minutes at room temperature, 9.9 mmol of N-hydroxypyrazole is added and the mixture is stirred for a further 14 hours. The reaction mixture is then hydrolyzed with 300 ml of 1N phosphoric acid and the resulting mixture is extracted several times with methyl tert-butyl ether. The organic phases are dried over sodium sulfate and evaporated down under reduced pressure. The residue is taken up in 40 ml of dimethylformamide, and 280 mg of sodium hydride (85% strength in paraffin, 10 mmol) is added. After the mixture has been stirred for 30 minutes at room temperature, 1.58 g (9 mmol) of 1-chloro-3,5-dimethoxy-s-triazine is added and the whole is stirred for 14 hours. The batch is introduced into 300 ml of 0.1N phosphoric acid, and extracted with diethyl ether. The ether phase is dried over sodium sulfate and evaporated down, and the residue is purified by column chromatography.

Workup

  1. stirringthe mixture is stirred for a further 14 hours
  2. extractionhydrolyzed with 300 ml of 1N phosphoric acid and the resulting mixture is extracted several times with methyl tert-butyl ether
  3. dry with materialThe organic phases are dried over sodium sulfate
  4. customevaporated down under reduced pressure
  5. stirringAfter the mixture has been stirred for 30 minutes at room temperature
  6. stirringthe whole is stirred for 14 hours
  7. extractionextracted with diethyl ether
  8. dry with materialThe ether phase is dried over sodium sulfate
  9. customevaporated down
  10. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-876c69db2b8146499f39252eada8512a
Source dataset
uspto-grants-1993_09
Patent number
US05246914

Reaction notes

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