Methyl bromoacetate → Methyl [3-[2-(4,5-diphenyl-2-thiazolyl)ethyl]phenoxy]acetate

HRID 1461755Notes

Reaction equation

HRID 1461755 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>C(#N)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[O:26][CH2:28][C:29]([O:31][CH3:32])=[O:30])[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 150069043-[2-(4,5-Diphenyl-2-thiazolyl)ethyl]phenol

Product 1

HCID 10477744Methyl [3-[2-(4,5-diphenyl-2-thiazolyl)ethyl]phenoxy]acetateYield 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-[2-(4,5-diphenyl-2-thiazolyl)-ethyl]phenol (3.65 g, 10 mmol), methyl bromoacetate (1.72 g, 1.06 mL, 11 mmol) potassium carbonate (1.69 g, 12 mmol) and acetonitrile (60 mL) was stirred at reflux for 90 minutes. The mixture was filtered and concentrated to leave an oil which was subjected to chromatography on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (2:1) afforded methyl [3-[2-(4,5-diphenyl-2-thiazolyl)-ethyl]phenoxy]acetate (3.63 g, 82%) as an oil.

Workup

  1. temperatureat reflux for 90 minutes
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customto leave an oil which
  5. washElution
  6. additionwith a mixture of hexanes and diethyl ether (2:1)

Sources & evidence

ORD record
ord-f036c1e836474b0b806e690e6087d578
Source dataset
uspto-grants-1991_12
Patent number
US05077305

Reaction notes

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