Iodoethane → (3,5-Dichloro-4-ethoxy-phenyl)-carbamic acid tert-butyl ester

HRID 649848Notes

Reaction equation

HRID 649848 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([OH:15])=[C:10]([Cl:16])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:24](I)[CH3:25]>CC(C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH2:24][CH3:25])=[C:10]([Cl:16])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22048528(3,5-Dichloro-4-hydroxy-phenyl)-carbamic Acid Tert-butyl Ester

Product 1

HCID 54404293(3,5-Dichloro-4-ethoxy-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (3,5-dichloro-4-hydroxy-phenyl)-carbamic acid tert-butyl ester (1.0 g) and potassium carbonate (1.0 g) in acetone (18 mL) is added ethyl iodide (0.36 mL) and the mixture is stirred for approximately 15 hours at room temperature. The solution is then filtered, concentrated under reduced pressure, and partitioned between ethyl acetate and water. The separated aqueous layer is further extracted twice with ethyl acetate, and the pooled organic extracts are washed successively with 10% aqueous sodium hydroxide, with water, and then dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the desired product as a tan solid.

Workup

  1. filtrationThe solution is then filtered
  2. concentrationconcentrated under reduced pressure
  3. custompartitioned between ethyl acetate and water
  4. extractionThe separated aqueous layer is further extracted twice with ethyl acetate
  5. washthe pooled organic extracts are washed successively with 10% aqueous sodium hydroxide, with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-6b3d63334cc84cdc80ced75494634ee7
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Reaction notes

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