Hydrochloric Acid → HCID 178459013, compound

HRID 275666Notes

Reaction equation

HRID 275666 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[C:7]([CH2:15][O:16][CH2:17][CH2:18][CH3:19])[C:8]([C:12](O)=[O:13])=[CH:9][CH:10]=2)[S:5](=[O:21])(=[O:20])[CH2:4][CH2:3]1.[CH3:23][N:24]1[C:28]([OH:29])=[CH:27][CH:26]=[N:25]1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C.C(OCC)(=O)C.O.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[C:7]([CH2:15][O:16][CH2:17][CH2:18][CH3:19])[C:8]([C:12]([C:27]3[CH:26]=[N:25][N:24]([CH3:23])[C:28]=3[OH:29])=[O:13])=[CH:9][CH:10]=2)[S:5](=[O:20])(=[O:21])[CH2:4][CH2:3]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 112903334,4-Dimethyl-8-propoxymethyl-1,1-dioxothiochromane-7-carboxylic acidHCID 178481816HCID 178481816, compound

Product 1

HCID 178459013HCID 178459013, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 22728543Water ethylacetateSolvent

Procedure

A solution of 0.6 g (1.84 mmol) of 4,4-dimethyl-8-propoxymethyl-1,1-dioxothiochromane-7-carboxylic acid, 0.18 g (1.84 mmol) of 1-methyl-5-hydroxypyrazole and 0.38 g (1.84 mmol) of N,N-dicyclohexylcarbodiimide in 20 ml of acetonitrile was stirred at room temperature for 12 hours. The reaction mixture was subsequently stirred into a mixture of ethyl acetate and 2% strength aqueous sodium carbonate solution, and the precipitate which formed was filtered off with suction. The organic phase of the filtrate was dried and the solvent was distilled off. The resulting residue was dissolved in 5 ml of 1,4-dioxane, 0.51 g (3.7 mmol) of potassium carbonate were added and the mixture was heated under reflux for 4 hours. After cooling, the reaction mixture was taken up in ethyl acetate/water, and the aqueous phase was adjusted to pH 3 using 2N hydrochloric acid and subsequently extracted with ethyl acetate. The extract was dried and the solvent was removed, giving a solid.

Workup

  1. customthe precipitate which formed
  2. filtrationwas filtered off with suction
  3. customThe organic phase of the filtrate was dried
  4. distillationthe solvent was distilled off
  5. dissolutionThe resulting residue was dissolved in 5 ml of 1,4-dioxane
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 4 hours
  8. temperatureAfter cooling
  9. extractionsubsequently extracted with ethyl acetate
  10. customThe extract was dried
  11. customthe solvent was removed
  12. customgiving a solid

Sources & evidence

ORD record
ord-ca51a17ce07a432b9c1203447caffd70
Source dataset
uspto-grants-2002_03
Patent number
US06352959B1

Reaction notes

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