Potassium Carbonate → HCID 20243557, compound

HRID 482937Notes

Reaction equation

HRID 482937 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:23]1([CH2:22][O:21][C:19](=[O:20])[CH2:18][NH:14][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:16][CH:15]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 517045Sodium AcetateHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 20243557HCID 20243557, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Benzyloxyaniline hydrochloride (5.893 g, 25 mmol) was added to a solution of benzyl bromoacetate (4.0 ml, 25 mmol) in 25 ml of dry dimethylformamide. Sodium acetate (2.051 g, 25 mmole) and 13.82 g (0.1 mole) of potassium carbonate were added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was extracted from water with three portions of ethyl acetate. The combined organic layers were washed with water and dried over sodium sulfate. The volatiles were removed, and the residue was purified by flash column chromatography on silica (LPS-1) (eluting with 15% ethyl acetate/hexane) to yield 5.64 g of the title compound.

Workup

  1. extractionThe reaction mixture was extracted from water with three portions of ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe volatiles were removed
  5. customthe residue was purified by flash column chromatography on silica (LPS-1) (eluting with 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3347f61dc3b34a26a79a07a7cd213d8d
Source dataset
uspto-grants-1986_03
Patent number
US04576749

Reaction notes

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