Water → 4-Chloro-2-ethoxy-1,3-benzothiazole

HRID 847798

Reaction equation

HRID 847798 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.ClC1S[C:15]2[CH:21]=CC=C(Cl)C=2N=1.[OH-:23].[Na+].O>C(O)C>[CH2:21]([O:23][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 771772,4-DichlorobenzothiazoleHCID 771782-Bromo-4-chlorobenzothiazole

Product 1

HCID 127660064-Chloro-2-ethoxy-1,3-benzothiazoleYield 92.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture (20.87 g, 0.1 mole) of 2-bromo-4-chlorobenzothiazole and 2,4-dichlorobenzothiazole and 94% sodium hydroxide (4.68 g, 0.11 mole) in 95% ethanol (200 c.c.) was heated under reflux for 1 hour. After cooling, water (250 c.c.) was added to the reaction solution, followed by ice-cooling. The deposited crystals were filtered and washed with water to obtain 19.86 g of 2-ethoxy-4-chlorobenzothiazole. Yield 92.9%, purity 98.9%, m.p. 43°-45° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureAfter cooling
  3. temperaturecooling
  4. filtrationThe deposited crystals were filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-cc1e255ac7744471b5cc99e783ebf1c7
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Linked notes

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