Water → 2-Phenoxyethyl acetate

HRID 420562Notes

Reaction equation

HRID 420562 reaction equation
ClC1C=CC2N=C(N3CCN(C[C:16]4[CH:17]=[C:18]([OH:23])[CH:19]=[C:20](C)[CH:21]=4)CC3)SC=2C=1.[C:26]([O:29][CH2:30][CH2:31]Br)(=[O:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O.C(OCC)(=O)C>[C:26]([O:29][CH2:30][CH2:31][O:23][C:18]1[CH:17]=[CH:16][CH:21]=[CH:20][CH:19]=1)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 57966425HCID 57966425, compound

Product 1

HCID 225682-Phenoxyethyl acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-{[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl}-5-methylphenol (0.50 g; 1.34 mmol), bromoethyl acetate (0.22 ml; 2.01 mmol) and cesium carbonate (0.65 g; 2.01 mmol) in anhydrous N,N-dimethylformamide (5 ml) was stirred at 50° C. for 17 hours. Water and ethyl acetate were added to the reaction solution and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=2:1) to give {3-[[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl]-5-methyl}+phenoxyethyl acetate as pale yellow oil (0.48 g; 78%).

Workup

  1. extractionextracted
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-83d9b45dddc44b3a928fc15a71a214e7
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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