2-Aminothiophenol → 2-(5-Bromopyridin-2-yl)benzo[d]thiazole

HRID 521545Notes

Reaction equation

HRID 521545 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]=O)=[N:14][CH:15]=1>C(O)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 667997612-(5-Bromopyridin-2-yl)benzo[d]thiazoleYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-aminothiophenol (5.01 g, 40.0 mmol), 5-bromo-2-formylpyridine (7.44 g, 40.0 mmol) and ethanol (40 mL) was heated to reflux (100° C.) while open to the atmosphere for 3 days. Upon confirming consumption of the starting materials by TLC (SiO2, 29:1 hexanes-acetone), the reaction was cooled to RT, the resulting mixture filtered and the filtrant washed copiously with ethanol to afford 9 (5.62 g, 48% yield) as an off-white solid.

Workup

  1. temperaturewas heated
  2. customconsumption of the starting materials by TLC (SiO2, 29:1 hexanes-acetone)
  3. temperaturethe reaction was cooled to RT
  4. filtrationthe resulting mixture filtered
  5. washthe filtrant washed copiously with ethanol

Sources & evidence

ORD record
ord-6c2ee52c359f42dfaba6bc55088a6c50
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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