Water → HCID 20524220, compound

HRID 1702993Notes

Reaction equation

HRID 1702993 reaction equation
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[O:6][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 819473HCID 819473, compound

Product 1

HCID 20524220HCID 20524220, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-methyl-N-phenylsalicylamide (13.5 g.), ethyl bromoacetate (10 g.) and anhydrous potassium carbonate (8.4 g.) in N,N-dimethylformamide (90 ml.) was stirred at room temperature for 7 hours. The resultant mixture was added to water and extracted with diethyl ether, and the extract was washed with 10% aqueous solution of sodium hydroxide and water in turn, dried over magnesium sulfate and then evaporated under reduced pressure to give oily ethyl 2-[2-(N-methyl-N-phenylcarbamoyl)phenoxy]acetate (18.23 g.).

Workup

  1. extractionextracted with diethyl ether
  2. washthe extract was washed with 10% aqueous solution of sodium hydroxide and water in turn
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fff93e2ff64146448dd8670b018639b9
Source dataset
uspto-grants-1982_09
Patent number
US04350692

Reaction notes

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