Hydrochloric Acid → HCID 69758873, compound

HRID 1359268Notes

Reaction equation

HRID 1359268 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1([CH3:20])O[C:17](=O)[CH2:16][C:14](=[O:15])[O:13]1.[N:21]1[CH:26]=CC=C[CH:22]=1.Cl.Cl[CH2:29]Cl>>[CH3:22][N:21]([CH:17]=[C:16]([C:8](=[O:9])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:14]([O:13][C:12]([CH3:20])([CH3:11])[CH3:29])=[O:15])[CH3:26]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6344DichloromethaneHCID 7679Phenylacetyl chlorideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 69758873HCID 69758873, compound

Procedure

Phenylacetyl chloride was slowly added dropwise into a mixture of 110 g of Meldrum's acid, 120 ml of pyridine and 500 ml of dichloromethane under stirring in an ice bath. After stirring overnight as it was, 650 ml of an aqueous 1.2 N hydrochloric acid solution was added to the mixture. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. To the residue was added 600 ml of tert-butanol, followed by heating under reflux for 3 hours. After cooling as it was, the solvent was removed while ethanol was added. To the residue were added 600 ml of toluene and 110 ml of N,N-dimethylformamidodimethylacetal, followed by heating under stirring for 2 hours in an oil bath kept at 100° C. while removing methanol by using Dean-Stark apparatus. The reaction solution was evaporated, and the residue was subjected to silica gel column chromatography using 50-70% ethyl acetate/hexane, to give 93 g of the target compound.

Workup

  1. stirringAfter stirring overnight as it
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed
  5. additionTo the residue was added 600 ml of tert-butanol
  6. temperatureby heating
  7. temperatureunder reflux for 3 hours
  8. temperatureAfter cooling as it
  9. customthe solvent was removed while ethanol
  10. additionwas added
  11. additionTo the residue were added 600 ml of toluene and 110 ml of N,N-dimethylformamidodimethylacetal
  12. temperatureby heating
  13. stirringunder stirring for 2 hours in an oil bath
  14. customkept at 100° C.
  15. customwhile removing methanol
  16. customThe reaction solution was evaporated

Sources & evidence

ORD record
ord-fa32e4bd231a40c9a3cfc24263d9da30
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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