Ethyl chloroacetate → HCID 14099036, compound

HRID 1198915Notes

Reaction equation

HRID 1198915 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[N:8][NH:7][C:6](=[O:17])[NH:5]1.Cl[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH3:3][CH:4]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:15]=2)=[N:8][NH:7][C:6](=[O:17])[NH:5]1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 135847670HCID 135847670, compound

Product 1

HCID 14099036HCID 14099036, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.12 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added to a solution of 0.55 g of 4,5-dihydro-5-methyl-6-(p-hydroxyphenyl)-1,2,4-triazin-3(2H)-one [prepared as described in step (a) above] dissolved in 6 ml of dimethylformamide, whilst ice-cooling and stirring, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, 0.33 g of ethyl chloroacetate was added. The mixture was then heated at 105° to 110° C. for 3 hours, whilst stirring. The dimethylformamide was then distilled off under reduced pressure, and the residue was diluted with water, after which the mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and then subjected to column chromatography through silica gel eluted with a 1:50 by volume mixture of ethanol and methylene chloride to give a brown oil. This oil was triturated with ethyl acetate to give crystals, which were recrystallized from ethyl acetate, to give 0.43 g of the title compound as pale yellow needles melting at 152°-153° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. temperatureThe mixture was then heated at 105° to 110° C. for 3 hours
  4. stirringwhilst stirring
  5. distillationThe dimethylformamide was then distilled off under reduced pressure
  6. additionthe residue was diluted with water
  7. extractionafter which the mixture was extracted with methylene chloride
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. washeluted with a 1:50 by volume mixture of ethanol and methylene chloride
  10. customto give a brown oil
  11. customThis oil was triturated with ethyl acetate
  12. customto give crystals, which
  13. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4d2e6bf5c83843f7b52633f5e2f1767a
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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