Sodium Hydroxide → 6-Bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazole-7-carboxylic acid

HRID 41266Notes

Reaction equation

HRID 41266 reaction equation
[Br:1][C:2]1[C:22]([C:23]([O:25]CC)=[O:24])=[C:5]2[S:6][CH:7]=[C:8]([C:9]3[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][O:18][CH3:19])=[CH:11][C:10]=3[O:20][CH3:21])[N:4]2[N:3]=1.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[C:22]([C:23]([OH:25])=[O:24])=[C:5]2[S:6][CH:7]=[C:8]([C:9]3[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][O:18][CH3:19])=[CH:11][C:10]=3[O:20][CH3:21])[N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58223417HCID 58223417, compound

Product 1

HCID 582234856-Bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazole-7-carboxylic acidYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (60.0 mL) solution of ethyl 6-bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazole-7-carboxylate (3.84 g, 8.45 mmol) was added a 5N aqueous solution of sodium hydroxide (5.07 mL, 25.3 mmol) and heated to reflux for two hours. After the reaction was completed, the solvent was distilled off under reduced pressure, water (30 mL) was added to the residue, a 5N aqueous solution of hydrochloric acid was added while cooling on ice so that the solution became acidic, and the precipitated solid was subjected to suction filtration and dried to obtain the title compound (3.4 g, 7.96 mmol).

Workup

  1. temperatureheated
  2. temperatureto reflux for two hours
  3. distillationthe solvent was distilled off under reduced pressure, water (30 mL)
  4. additionwas added to the residue
  5. additiona 5N aqueous solution of hydrochloric acid was added
  6. temperaturewhile cooling on ice so that the solution
  7. filtrationthe precipitated solid was subjected to suction filtration
  8. customdried

Sources & evidence

ORD record
ord-e224b37d16dc4249bbf8880f5ab423bd
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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