1,3-Dibromopropane → HCID 11616710, compound

HRID 131622Notes

Reaction equation

HRID 131622 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([OH:18])[CH:11]=3)=[N:7][C:6]=2[CH:19]=1.[C:20]([O-:23])([O-])=O.[K+].[K+].Br[CH2:27]CCBr>CC#N>[CH3:20][O:23][C:11]1[C:12]([O:18][CH3:27])=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:19][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 404992HCID 404992, compound

Product 1

HCID 11616710HCID 11616710, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole 5 (0.15 g, 0.55 mmol) in CH3CN (30 ml) were added K2CO3 (0.11 g, 0.82 mmol) and 1,3-dibromopropane (0.28 ml, 2.74 mmol), and the mixture was heated under reflux at 80° C. for 24 hours. The reaction mixture was allowed to cool at room temperature and then concentrated in vacuum. The residue was taken up with CHCl3 (30 ml), and the CHCl3 layer was washed with 0.2N NaOH aq (30 ml×2), then dried and concentrated in vacuum. The residue was purified by column chromatography on silica gel (chloroform), followed by recrystallisation from ethanol/water to give a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool at room temperature
  3. concentrationconcentrated in vacuum
  4. washthe CHCl3 layer was washed with 0.2N NaOH aq (30 ml×2)
  5. customdried
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by column chromatography on silica gel (chloroform)
  8. customfollowed by recrystallisation from ethanol/water
  9. customto give a white solid

Sources & evidence

ORD record
ord-91885e302fb54d809decf8fb2d47aa6f
Source dataset
uspto-grants-2008_06
Patent number
US07384966B2

Reaction notes

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