Sodium Bicarbonate → 6-Hydroxybenzothiazole

HRID 240544Notes

Reaction equation

HRID 240544 reaction equation
Br.C[O:3][C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][S:10][C:6]=2[CH:5]=1.C([O-])(O)=O.[Na+]>Br.O>[S:10]1[C:6]2[CH:5]=[C:4]([OH:3])[CH:12]=[CH:11][C:7]=2[N:8]=[CH:9]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 66937320HCID 66937320, compound

Product 1

HCID 1518116-HydroxybenzothiazoleYield 57%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

6-methoxybenzo[d]thiazole hydrobromide (1.00 g, 4.06 mmol) was dissolved in aqueous hydrobromide (10 mL of 48% solution). After heating to reflux for 10 hours, the mixture was cooled in an ice bath and diluted with water (50 mL). After adjusting the pH to 8 with the slow addition of solid NaHCO3, the mixture was filtered, washing the solid with water and air-drying to provide the product (0.35 g, 57%) as white solid.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 10 hours
  3. temperaturethe mixture was cooled in an ice bath
  4. filtrationthe mixture was filtered
  5. washwashing the solid with water
  6. customair-drying

Sources & evidence

ORD record
ord-edab8c8e601d4ef8b50aaf51fc73971f
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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