Acetone → HCID 53796507, compound

HRID 1702896Notes

Reaction equation

HRID 1702896 reaction equation
[Na+].[O:2]=[C:3]1[NH:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O-:23])=[O:22].[CH3:24]C(C)=O.[OH-].[K+].CI>O>[CH3:24][N:7]1[CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:3]1=[O:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 70520228HCID 70520228, compound

Product 1

HCID 53796507HCID 53796507, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3.2 g of 8-(2-oxo-5-phenyl-4-imidazolin-1-yl) caprylic acid sodium salt (preparation see German patent application No. P 29 34 746.4) are suspended in 20 cc. of acetone together with 2.8 g of pulverized potassium hydroxide. The mixture is refluxed and converted into a homogenous solution by the addition of some drops of water. Thereafter, 2.8 g of methyliodide are added at boiling temperature, the mixture is refluxed for 30 minutes and cooled to room temperature. After cooling, so much of water is added that precipitated solids are dissolved. The solution is stirred at room temperature for 4 hours, is acidified and diluted with water until the crude acid is separated as oil. The oil is dissolved in a small amount of chloroform, the chloroform phase is washed with water several times and is finally extracted with 5% soda lye. The soda lye extract is washed with chloroform, the aqueous solution is acidified with dilute hydrochloric acid and is separated from the acid precipitated as an oil. Purification occurs by chromatography on silicic acid gel using a mixture of chloroform and methanol as eluant.

Workup

  1. temperatureThe mixture is refluxed
  2. temperaturethe mixture is refluxed for 30 minutes
  3. additionis added
  4. customthat precipitated solids
  5. dissolutionare dissolved
  6. additiondiluted with water until the crude acid
  7. customis separated as oil
  8. dissolutionThe oil is dissolved in a small amount of chloroform
  9. washthe chloroform phase is washed with water several times
  10. extractionis finally extracted with 5% soda lye
  11. extractionThe soda lye extract
  12. washis washed with chloroform
  13. customis separated from the acid
  14. customprecipitated as an oil
  15. customPurification
  16. additiona mixture of chloroform and methanol as eluant

Sources & evidence

ORD record
ord-ff7dbc473a2943aa8f647effa044bdab
Source dataset
uspto-grants-1982_09
Patent number
US04349684

Reaction notes

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