Dimethylformamide → HCID 21072928, compound

HRID 1373263Notes

Reaction equation

HRID 1373263 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[CH2:8][NH:9][C:10](=[O:12])[O-:11].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:7]([O:12][C:10]([NH:9][CH2:8][C:7]1[CH:6]=[C:5]([CH:15]=[CH:14][CH:13]=1)[O:4][C:3]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:2]=1[NH:1][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:11])([CH3:13])([CH3:8])[CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 86760357HCID 86760357, compound

Product 1

HCID 21072928HCID 21072928, compoundYield 131.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl[3-(2-amino-5-chlorophenoxy)benzylcarbamate (5.2 g, 15 mmols), ethyl bromoacetate (3.3 ml, 30 mmols), potassium carbonate (2.1 g, 15 mmols) and N,N-dimethylformamide (30 ml) was stirred at 60° C. for 12 hours. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give an oil of ethyl 2-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]aminoacetate (4.3 g, 66%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThis was concentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-246aa91f89f74c39b156ba45ab619614
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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