Potassium Carbonate → Tert-butyl {2-[(1-chloro-6-cyanonaphthalen-2-yl)oxy]ethyl}carbamate

HRID 1400301Notes

Reaction equation

HRID 1400301 reaction equation
[Cl:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13]#[N:14])=[CH:7]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>CC(C)=O>[Cl:1][C:2]1[C:3]2[C:8](=[CH:7][C:6]([C:13]#[N:14])=[CH:5][CH:4]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 681514405-Chloro-6-hydroxynaphthalene-2-carbonitrile

Product 1

HCID 86709755Tert-butyl {2-[(1-chloro-6-cyanonaphthalen-2-yl)oxy]ethyl}carbamateYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-chloro-6-hydroxynaphthalene-2-carbonitrile (1.5 mmol) and K2CO3 (3 mmol) in acetone was added tert-butyl (2-bromoethyl)carbamate (2.1 mmol). The resulting mixture was heated at reflux overnight. After TLC control (n-hexane/ethyl acetate 65:35), solvent was evaporated in vacuo and the residue was dissolved in 15 mL of ethyl acetate and washed with water (3×5 mL), brine (10 mL) and dried over Na2SO4. The evaporation of solvent afforded tert-butyl {2-[(1-chloro-6-cyanonaphthalen-2-yl)oxy]ethyl}carbamate as a brown solid (81% yield) which was used without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customAfter TLC control (n-hexane/ethyl acetate 65:35), solvent was evaporated in vacuo
  4. dissolutionthe residue was dissolved in 15 mL of ethyl acetate
  5. washwashed with water (3×5 mL), brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. customThe evaporation of solvent

Sources & evidence

ORD record
ord-55098ed6616b4453be215c58e7be71b9
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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