Hydrochloric Acid → 6-Bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazole

HRID 41267

Reaction equation

HRID 41267 reaction equation
[Br:1][C:2]1[C:22](C(O)=O)=[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.Cl>O1CCOCC1>[Br:1][C:2]1[CH:22]=[C:5]2[S:6][CH:7]=[C:8]([C:9]3[C:10]([O:20][CH3:21])=[CH:11][C:12]([CH2:17][O:18][CH3:19])=[CH:13][C:14]=3[O:15][CH3:16])[N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58223485HCID 58223485, compound

Product 1

HCID 582234186-Bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazoleYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 1,4-dioxane (90.0 mL) solution of 6-bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazole-7-carboxylic acid (5.00 g, 11.7 mmol) was added concentrated hydrochloric acid (14.9 mL) and the mixture was heated to reflux for 13 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, water (50 mL) was added to the residue, and the precipitated solid was subjected to suction filtration and dried to obtain the title compound (1.12 g, 2.92 mmol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 13 hours
  3. distillationthe solvent was distilled off under reduced pressure, water (50 mL)
  4. additionwas added to the residue
  5. filtrationthe precipitated solid was subjected to suction filtration
  6. customdried

Sources & evidence

ORD record
ord-7e5e6bca274745aa8f6228e6e192d79a
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Linked notes

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