Hydrochloric Acid → HCID 90092924, compound

HRID 1774575Notes

Reaction equation

HRID 1774575 reaction equation
[Br:1][C:2]1[C:3]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[N:4][N:5]([CH3:12])[C:6]=1[CH:7](OC)[O:8]C.Cl.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[C:3]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[N:4][N:5]([CH3:12])[C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90092962HCID 90092962, compound

Product 1

HCID 90092924HCID 90092924, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-[4-bromo-5-(dimethoxymethyl)-1-methyl-1H-pyrazol-3-yl]-1,3-thiazole (8d) (586 mg, 1.84 mmol) in tetrahydrofuran (15 mL) was treated with 1N hydrochloric acid (2.26 mL) and the mixture was stirred at 50° C. for 5 hours. The reaction was cooled to room temperature and then neutralized with 1N sodium hydroxide (2.26 mL). The resulting mixture was extracted with ethyl acetate (2×15 mL) and the organic layer was dried over sodium sulfate and concentrated in vacuo to provide 4-bromo-1-methyl-3-(1,3-thiazol-2-yl)-1H-pyrazole-5-carbaldehyde (8e) (480 mg, 1.76 mmol, 96%) which was used without further purification.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate (2×15 mL)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f40669ca409346a3b946952efef8f891
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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