Ethyl bromoacetate → 5-Octyl-5-(ethoxycarbonylmethyl)barbituric acid

HRID 1249682Notes

Reaction equation

HRID 1249682 reaction equation
[CH2:1]([CH:9]1[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11][C:10]1=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O>[CH2:1]([C:9]1([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11][C:10]1=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 260794Octyl barbituric acid

Product 1

HCID 98621425-Octyl-5-(ethoxycarbonylmethyl)barbituric acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.05 g of 5-octylbarbituric acid (preparation 7) are dissolved in 25 ml of dimethylformamide, 1.16 g of sodium carbonate are added. Ethyl bromoacetate (2.25 ml) is added dropwise to the reaction mixture in 5 minutes, then the mixture is kept at room temperature under stirring for about 3 hours. The reaction mixture is then partitioned between 400 ml of water, 17 ml of 1 N hydrochloric acid and 150 ml of ethyl acetate. The organic phase is separated and washed with 150 ml of water and 100 ml of brine, then it is dried over sodium sulfate. The aqueous phases are extracted with 100 ml of ethyl acetate and the organic extracts are pooled, dried over sodium sulfate and evaporated to dryness, to give 6.5 g an oily residue. This residue is purified by silica gel chromatography (eluant methylene chloride/ethyl acetate 9 1) to give 3.87 g of the product.

Workup

  1. customis kept at room temperature
  2. customThe reaction mixture is then partitioned between 400 ml of water, 17 ml of 1 N hydrochloric acid and 150 ml of ethyl acetate
  3. customThe organic phase is separated
  4. washwashed with 150 ml of water and 100 ml of brine
  5. dry with materialit is dried over sodium sulfate
  6. extractionThe aqueous phases are extracted with 100 ml of ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-3c3411771cd94c18a68188968c511f97
Source dataset
uspto-grants-2002_01
Patent number
US06335332B1

Reaction notes

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