1,4-Dibromobutane → HCID 68630196, compound

HRID 1750093Notes

Reaction equation

HRID 1750093 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][CH2:15]Br.C([O-])([O-])=O.[K+].[K+]>CCO>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][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 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 35965065-Benzothiazolol

Product 1

HCID 68630196HCID 68630196, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (206 mg, 1.4 mmol), 1,4-dibromobutane (0.5 mL, 4.2 mmol) and anhydrous K2CO3 (193 mg, 1.4 mmol) in EtOH (20 mL) was heated to reflux and stirred overnight. The yellow solid was filtered and purified by column chromatography (elution with PE/EtOAc=4:1) to afford 5-(4-bromobutoxy)benzo[d]thiazole (intermediate 26) (108 mg, 39%) as a yellow oil. HPLC: 99%, RT 3.426 min. MS (ESI) m/z 288.0 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-a02c0d8cf99e480684f93acaaf04fb81
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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