1,3-Dibromopropane → 5-(3-Bromopropoxy)benzo[d]thiazole

HRID 1750094Notes

Reaction equation

HRID 1750094 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.[Br:11][CH2:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>CCO>[Br:11][CH2:12][CH2:13][CH2:14][O:10][C:8]1[CH:7]=[CH:6][C:5]2[S:1][CH:2]=[N:3][C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 35965065-Benzothiazolol

Product 1

HCID 666315515-(3-Bromopropoxy)benzo[d]thiazoleYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (1 g, 6.6 mmol), 1,3-dibromopropane (1.83 mL, 18 mmol), anhydrous K2CO3 (828 mg, 6.0 mmol) and EtOH (20 mL) was heated to reflux and stirred overnight. The yellow solid was filtered and purified by column chromatography (elution with PE/EtOAc=3:1) to afford 5-(3-bromopropoxy)benzo[d]thiazole (intermediate 27) (543 mg, 33%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationThe yellow solid was filtered
  4. custompurified by column chromatography (elution with PE/EtOAc=3:1)

Sources & evidence

ORD record
ord-87fab5765c9e4b60bdfa7972a25b0bb7
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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