Hydrochloric Acid → HCID 57912454, compound

HRID 1971781Notes

Reaction equation

HRID 1971781 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH2:10][O:11][CH3:12])[CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[C:15]1[N:16]2[N:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:17]2[S:18][CH:19]=1.[N:25]([O-])=[O:26].[Na+].[OH-].[Na+]>C(OCC)(=O)C.O>[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH2:10][O:11][CH3:12])[CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[C:15]1[N:16]2[N:22]=[C:21]([O:23][CH3:24])[C:20]([N:25]=[O:26])=[C:17]2[S:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 579124443-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazole

Product 1

HCID 57912454HCID 57912454, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of water and 5N hydrochloric acid (1:4, 70 mL) was added to 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazole (2.17 g, 6.47 mmol), and then sodium nitrite (1.06 g, 15.3 mmol) was added at 0° C. and the mixture was stirred for 1 hour. Aqueous 5N sodium hydroxide and ethyl acetate were added to the mixture at room temperature. After thoroughly shaking the mixture, the organic layer was separated and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (2.34 g, 6.44 mmol).

Workup

  1. stirringAfter thoroughly shaking the mixture
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was then filtered
  5. distillationthe solvent in the filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b7350403ef3a4299b2552e2ead119e10
Source dataset
uspto-grants-2013_04
Patent number
US08431603B2

Reaction notes

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