Water → 2-n-Propoxy-4-chlorobenzothiazole

HRID 847799

Reaction equation

HRID 847799 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:16]=2N=1.[OH-:23].[Na+].O>C(O)CC>[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)[CH2:15][CH3:16]

Participants

6

Reactant 4

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

Product 1

HCID 127660072-n-Propoxy-4-chlorobenzothiazoleYield 97.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture (11.30 g, 0.05 mole) of 2-bromo-4-chlorobenzothiazole and 2,4-dichlorobenzothiazole and 94% sodium hydroxide (2.34 g, 0.055 mole) in n-propanol (100 c.c.) was heated under reflux for 1 hour. Water was added and the alcohol was distilled azeotropically together with water. The resulting oily substance was extracted with chloroform, and the chloroform layer was washed with water. The solvent was removed under reduced pressure to obtain 11.12 g of 2-n-propoxy-4-chlorobenzothiazole as a yellow viscous liquid. Yield 97.7%, purity 98.9%, b.p. 106°-108° C./0.12 mmHg.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationthe alcohol was distilled azeotropically together with water
  3. extractionThe resulting oily substance was extracted with chloroform
  4. washthe chloroform layer was washed with water
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-705986d35b744ee8a86accc645a337d5
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Linked notes

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