Sodium hydride → HCID 13269938, compound

HRID 1649598Notes

Reaction equation

HRID 1649598 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[N:13][C:14](=[O:16])[CH:15]=2)=[CH:7][CH:6]=1.S(O[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]([C:37]1[CH:38]([C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([Cl:55])[C:50]=2[Cl:56])[C:39]([C:45]([O:47][CH3:48])=[O:46])=[C:40]([CH3:44])[NH:41][C:42]=1[CH3:43])=[O:36])(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:12][N:13]=[C:14]([O:16][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]([C:37]3[CH:38]([C:49]4[CH:54]=[CH:53][CH:52]=[C:51]([Cl:55])[C:50]=4[Cl:56])[C:39]([C:45]([O:47][CH3:48])=[O:46])=[C:40]([CH3:44])[NH:41][C:42]=3[CH3:43])=[O:36])[CH:15]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19380105HCID 19380105, compoundHCID 86739134HCID 86739134, compound

Product 1

HCID 13269938HCID 13269938, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 0.262 g of sodium hydride (55% dispersion in mineral oil) in 10 ml of N,N-dimethylformamide, 1.33 g (7 mmole) of 3-p-methoxyphenyl-5-pyrazolone was added portionwise with stirring under ice cooling. To the above mixture was added dropwise a solution of 3.05 g (5 mmole) of 1,4-dihydro-2,6-dimethyl-4-(2,3-dichlorophenyl)-3-methoxycarbonylpyridine-5-carboxylic acid 6-tosyloxyhexyl ester in 7 ml of N,N-dimethylformamide at 0° to 10° C. with stirring and then the mixture was heated at 80° C. for 3 hours. The resulting reaction mixture was poured into ice water, and the precipitate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and then evaporated in vacuo to obtain an oily residue. The residue was purified by silica gel column chromatography using a mixed solution of chloroform-methanol (the ratio by volume of 100:1) as an eluent, and the fractions containing desired compound were collected and evaporated in vacuo to dryness to give white crystalline residue. The residue was recrystallized from a mixed solution of ethyl acetate-normal hexane to give 1.87 g (yield 59.0%) of the 1,4-dihydro-2,6-dimethyl-4-(2,3-dichlorophenyl)-3-methoxycarbonylpyridine-5-carboxylic acid 6-(5-p-methoxyphenyl-3-pyrazolyloxy)hexyl ester as colorless needles.

Workup

  1. additionwas added portionwise
  2. stirringwith stirring
  3. customThe resulting reaction mixture
  4. extractionthe precipitate was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customto obtain an oily residue
  9. customThe residue was purified by silica gel column chromatography
  10. additionthe fractions containing desired compound
  11. customwere collected
  12. customevaporated in vacuo to dryness
  13. customto give white crystalline residue
  14. customThe residue was recrystallized from a mixed solution of ethyl acetate-normal hexane

Sources & evidence

ORD record
ord-baab7e440ecd4d0c9398b75a17310b17
Source dataset
uspto-grants-1983_11
Patent number
US04418197

Reaction notes

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