Hydrochloric Acid → HCID 57912453, compound

HRID 1971780Notes

Reaction equation

HRID 1971780 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[C:7]([O:14][CH3:15])[C:6]=1[C:16]1[N:17]2[N:23]=[C:22]([O:24][CH3:25])[C:21]([C:26]([O:28]CC)=[O:27])=[C:18]2[S:19][CH:20]=1.Cl>C(O)C>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[C:7]([O:14][CH3:15])[C:6]=1[C:16]1[N:17]2[N:23]=[C:22]([O:24][CH3:25])[C:21]([C:26]([OH:28])=[O:27])=[C:18]2[S:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57912457HCID 57912457, compound

Product 1

HCID 57912453HCID 57912453, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After adding ethanol (124 mL) and aqueous 5N sodium hydroxide (11 mL, 55 mmol) in that order to ethyl 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazole-7-carboxylate (2.8 g, 6.89 mmol), the mixture was heated to reflux for 2 hours. Aqueous 5N hydrochloric acid (11 mL) was then added to the mixture while cooling on ice, and the solvent in the mixture was distilled off under reduced pressure. Water was added to the residue, and the precipitated solid was collected by filtration, washed with water and dried under reduced pressure to obtain the title compound (2.52 g, 6.66 mmol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturewhile cooling on ice
  4. distillationthe solvent in the mixture was distilled off under reduced pressure
  5. additionWater was added to the residue
  6. filtrationthe precipitated solid was collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-806964e30a9240f683e215c136360b6c
Source dataset
uspto-grants-2013_04
Patent number
US08431603B2

Reaction notes

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