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

HRID 486013Notes

Reaction equation

HRID 486013 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([OH:17])[C:13]=1[C:14]([OH:16])=[O:15].O[N:19]1[CH:23]=[CH:22][CH:21]=[N:20]1.[H-].[Na+].Cl[N:27]1[CH2:32][N:31]([O:33][CH3:34])[CH2:30][N:29]([O:35][CH3:36])[CH2:28]1.P(=O)(O)(O)O>O1CCCC1.CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([C:14]([O:16][N:19]2[CH:23]=[CH:22][CH:21]=[N:20]2)=[O:15])=[C:12]([O:17][N:27]2[CH2:32][N:31]([O:33][CH3:34])[CH2:30][N:29]([O:35][CH3:36])[CH2:28]2)[CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 24758Sodium hydrideHCID 30167331-hydroxy-1H-pyrazoleHCID 148178396-(2-Methylphenyl)-salicylic acidHCID 190972191-Chloro-3,5-dimethoxy-s-triazine

Product 1

HCID 573116216-(2-Methylphenyl)-2-(3,5-dimethoxy-s-triazin-1-yloxy)-1-[(1-pyrazolyl)-oxycarbonyl]-benzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.75 g (10.8 mmol) of N,N'-carbonylbisimidazole is added to a solution of 2.12 g (10 mmol) of 6-(2-methylphenyl)-salicylic 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 mixture is then hydrolyzed with 300 ml of 1N phosphoric acid and extracted several times with methyl tert-butyl ether. The organic phases are combined, dried over sodium sulfate and evaporated down under reduced pressure. The residue is taken up with 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 mixture stirred for 14 hours. It is then 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. additionis added
  2. extractionhydrolyzed with 300 ml of 1N phosphoric acid and extracted several times with methyl tert-butyl ether
  3. dry with materialdried over sodium sulfate
  4. customevaporated down under reduced pressure
  5. additionis added
  6. stirringAfter the mixture has been stirred for 30 minutes at room temperature
  7. stirringthe mixture stirred for 14 hours
  8. extractionextracted with diethyl ether
  9. dry with materialThe ether phase is dried over sodium sulfate
  10. customevaporated down
  11. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-2fda91be2e244671b52a7af6898bebab
Source dataset
uspto-grants-1994_03
Patent number
US05290755

Reaction notes

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