Methanol → 4-Chloro-2-methoxybenzothiazole

HRID 847795

Reaction equation

HRID 847795 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1.[OH-:12].[Na+].[CH3:14]O>O>[CH3:14][O:12][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 771782-Bromo-4-chlorobenzothiazole

Product 1

HCID 41419694-Chloro-2-methoxybenzothiazoleYield 93.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromo-4-chlorobenzothiazole (6.21 g, 0.025 mole) and 94% sodium hydroxide (1.57 g, 0.037 mole) were added to methanol (100 c.c.), and the mixture was heated under reflux for 30 minutes. After cooling, water (100 c.c.) was added to the reaction solution, followed by ice-cooling. The deposited crystals were filtered and washed with water to obtain 4.68 g of 2-methoxy-4-chlorobenzothiazole. Yield 93.8%, purity 99.3%, m.p. 55°-57° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. temperaturecooling
  5. filtrationThe deposited crystals were filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-6e26b00862f84353ab12bbfba02506a2
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Linked notes

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