Phenethyl bromide → 3-(2-phenylethyl)-1,3-benzothiazol-2(3H)-one

HRID 234165

Reaction equation

HRID 234165 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[H-].[Na+].[H][H].[C:15]1([CH2:21][CH2:22]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:22]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][C:2]1=[O:10])[CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 7666Phenethyl bromideHCID 13625BenzothiazoloneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 10931463-(2-phenylethyl)-1,3-benzothiazol-2(3H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1aB) Benzothiazolin-2-one (5.15 g, 34.1 mmol) was dissolved in dimethylformamide (100 ml) and to the solution was added 60% sodium hydride (1.36 g, 34.1 mmol) which was stirred at room temperature until generation of hydrogen gas stopped. Then β-phenylethylbromide (4.89 ml, 35.8 mmol) was added to the solution which was stirred at room temperature for 17 hours. To the reaction solution was added a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed in turn with a saturated sodium bicarbonate solution and saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The crude product thus obtained was purified by subjecting it to silica gel column chromatography to give 6.49 g of 3-phenethylbenzothiazoline-2-one as a white amorphous powder form n-hexane/ethyl (4:1)-eluted fraction (yield: 80%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed in turn with a saturated sodium bicarbonate solution and saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe crude product thus obtained
  6. customwas purified

Sources & evidence

ORD record
ord-456553774f75411b9d86aa476cb84047
Source dataset
uspto-grants-1997_01
Patent number
US05594144

Linked notes

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