Triethylamine → HCID 178463111, compound

HRID 1168131Notes

Reaction equation

HRID 1168131 reaction equation
[CH:1]1([N:4]2[C:8](=[O:9])[N:7]([CH2:10][C:11]3[C:12]([Cl:21])=[C:13]([CH:17]=[CH:18][C:19]=3[Cl:20])[C:14](Cl)=[O:15])[N:6]=[N:5]2)[CH2:3][CH2:2]1.[CH2:22]([N:24]1[C:28]([OH:29])=[CH:27][CH:26]=[N:25]1)[CH3:23].C(N(CC)CC)C>ClCCCl>[CH:1]1([N:4]2[C:8](=[O:9])[N:7]([CH2:10][C:11]3[C:12]([Cl:21])=[C:13]([CH:17]=[CH:18][C:19]=3[Cl:20])[C:14]([C:27]3[CH:26]=[N:25][N:24]([CH2:22][CH3:23])[C:28]=3[OH:29])=[O:15])[N:6]=[N:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12993703HCID 12993703, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 178463111HCID 178463111, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A 1,2-dichloroethane solution of 3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichloroberizoyl chloride (0.70 g) was added drop by drop to the solution of 1-ethyl-5-hydroxypyrazole (0.24 g) and triethylamine (0.24 g) in 1,2-dichloroethane (4 ml) at 5° C. and the mixture was stirred at room temperature for 6 hours. After reaction it was extracted with dicbloromethane (100 ml), washed with diluted hydrochloric acid and aqueous solution of sodium hydrogen carbonate and then dried with anhydrous magnesium sulfate. The residue, obtained by distilling off the solvent, was dissolved in 1,4-dioxane (8 ml), added with potassium carbonate (0.38 g) and refluxed by heating for 3 hours. After the solvent was distilled off, the residue was teated with an aqueous solution of potassium carbonate and washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate (150 ml). The organic layer was washed with saturated salt water and dried with anhydrous magnesium sulfate. By distilling off the ethyl acetate, the objective 4-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorobenzoyl}-5-hydroxy-1-ethylpyrazole (0.73 g, 88% yield from 3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorobenzoic acid) was obtained. nD20: 1.5510.

Workup

  1. customAfter reaction it
  2. extractionwas extracted with dicbloromethane (100 ml)
  3. washwashed with diluted hydrochloric acid and aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe residue, obtained
  6. distillationby distilling off the solvent
  7. dissolutionwas dissolved in 1,4-dioxane (8 ml)
  8. additionadded with potassium carbonate (0.38 g)
  9. temperaturerefluxed
  10. temperatureby heating for 3 hours
  11. distillationAfter the solvent was distilled off
  12. washwashed with ethyl acetate
  13. extractionextracted with ethyl acetate (150 ml)
  14. washThe organic layer was washed with saturated salt water
  15. dry with materialdried with anhydrous magnesium sulfate
  16. distillationBy distilling off the ethyl acetate

Sources & evidence

ORD record
ord-39ea21e32d44480fbf5ccb80ac66219f
Source dataset
uspto-grants-2003_09
Patent number
US06624121B1

Reaction notes

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