1-Bromo-3-chloropropane → 6-Chloro-3-(3-chloropropyl)-2(3H)-benzothiazolone

HRID 2259405Notes

Reaction equation

HRID 2259405 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[CH:7][S:8](=O)[C:4]=2[CH:3]=1.C([O-])([O-])=[O:13].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22]>CC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([CH2:19][CH2:20][CH2:21][Cl:22])[C:7](=[O:13])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 53400706HCID 53400706, compound

Product 1

HCID 190035086-Chloro-3-(3-chloropropyl)-2(3H)-benzothiazoloneYield 93.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 6-chloro-benzothiazolone (VIII) (55.7 g, 0.3 mol), K2CO3 (62.1 g, 0.45 mol) and 1-bromo-3-chloropropane (IX) (71 g, 0.45 mol) in acetone (600 ml) was refluxed for 16 hours. After cooling, the inorganic substance was filtered off and washed dichloromethane. The filtrate and washings were combined and evaporated in vacuo. The residue was washed with hexane and recrystallized from dichloromethane to obtain compound (X) (73.5 g, yield=93.4%) as colorless needle-shaped crystals.

Workup

  1. temperatureAfter cooling
  2. filtrationthe inorganic substance was filtered off
  3. washwashed dichloromethane
  4. customevaporated in vacuo
  5. washThe residue was washed with hexane
  6. customrecrystallized from dichloromethane

Sources & evidence

ORD record
ord-fc6c6655846d4acfaf8a67555ceb05d1
Source dataset
uspto-grants-1995_12
Patent number
US05473066

Reaction notes

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