Potassium Carbonate → 2-(4-Chloronaphthalen-1-yl)oxyacetamide

HRID 56290

Reaction equation

HRID 56290 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.Br[CH2:14][C:15]([NH2:17])=[O:16].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:14][C:15]([NH2:17])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117874-Chloro-1-naphtholHCID 696322-Bromoacetamide

Product 1

HCID 3029082-(4-Chloronaphthalen-1-yl)oxyacetamideYield 49.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chloronaphthalen-1-ol (3.57 g, 20.0 mmol), 2-bromoacetamide (2.76 g, 20.0 mmol) and K2CO3 (5.53 g, 40.0 mmol) in acetone (40 mL) was stirred at 70° C. overnight. The mixture was cooled to rt and filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (2.32 g, 49%).

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-1e15743c027b4fababa33b26a6f003e1
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

Loading…