Acetic Acid → HCID 24772784, compound

HRID 2243219Notes

Reaction equation

HRID 2243219 reaction equation
Cl.[NH2:2][OH:3].CN(/[CH:7]=[N:8]/[C:9]([C:11]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23][C:24]3[CH:29]=[CH:28][C:27]([N:30]4[C:34](=O)[NH:33][C:32]([CH3:36])=[N:31]4)=[CH:26][CH:25]=3)[CH:18]=2)[CH2:16][CH2:15]O[CH2:13][CH2:12]1)=O)C.[O:37]1[CH2:42]COCC1.[C:43](O)(=O)C.[OH-:47].[Na+]>CCCCCC.C(OCC)(=O)C>[CH3:34][N:33]1[C:32]([CH3:36])=[N:31][N:30]([C:27]2[CH:26]=[CH:25][C:24]([S:23][C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([C:11]4([C:9]5[O:3][N:2]=[C:7]([CH3:43])[N:8]=5)[CH2:12][CH2:13][O:47][CH2:15][CH2:16]4)[CH:18]=3)=[CH:29][CH:28]=2)[C:42]1=[O:37]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 443297Hydroxyamine hydrochlorideHCID 178433912HCID 178433912, compound

Product 1

HCID 24772784HCID 24772784, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of hydroxylamine hydrochloride (0.522 g, 7.52 mmol) in sodium hydroxide (1 M, 10 mL) was added to N-[(1E)-1-(dimethylamino)ethylidene]-4-(3-{[4-(3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phenyl]thio}phenyl)tetrahydro-2H-pyran-4-carboxamide (1.20 g, 2.51 mmol) (example 11). 1,4-dioxane (7.5 mL) followed by glacial acetic acid (10 mL) were added to the mixture, the reaction mixture stirred for about 30 minutes at room temperature and then heated at 90° C. for about 10 hours. The solvent was evaporated under vacuum and a saturated solution of potassium carbonate was added until the solution became basic. The reaction mixture was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulphate, filtered and the solvent evaporated under vacuum to afford a thick oil residue which upon column chromatography over silica gel using ethyl acetate and hexane (4:1) gave the title compound as a thick oil. Yield: 0.60 g

Workup

  1. additionwere added to the mixture
  2. temperatureheated at 90° C. for about 10 hours
  3. customThe solvent was evaporated under vacuum
  4. additiona saturated solution of potassium carbonate was added until the solution
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customthe solvent evaporated under vacuum
  10. customto afford a thick oil residue which upon column chromatography over silica gel

Sources & evidence

ORD record
ord-dab12c2618394be8a4d1bf81b0dce339
Source dataset
uspto-grants-2010_03
Patent number
US07674811B2

Reaction notes

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