Hydrochloric Acid → HCID 23350230, compound

HRID 2057858Notes

Reaction equation

HRID 2057858 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10](OCC)[CH:11]=C=O)=[CH:4][C:3]=1[N:17]1[C:25](=[O:26])[N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][C:19]2=[N:18]1.Cl.O1CCOCC1.[C:34](=[O:37])(O)[O-:35].[Na+]>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([C:34]([OH:35])=[O:37])[CH3:11])=[CH:4][C:3]=1[N:17]1[C:25](=[O:26])[N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][C:19]2=[N:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 86737096HCID 86737096, compound

Product 1

HCID 23350230HCID 23350230, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.8 Parts of 2-[2,4-dichloro-5-(1-ethoxy-carbonylethoxy)-phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-one, 20.6 parts of concentrated hydrochloric acid (38%) and 175 parts of dioxane were combined and heated to 80° for 30 hours. After cooling the solution was poured into 750 parts of water. The pH of the solution was raised to 8-9 by addition of solid sodium bicarbonate. The aqueous solution of the product was then extracted three times with 250 parts of methylene chloride. The organic extracts were discarded. The aqueous solution of the product was then acidified to pH 1 by addition at concentrated hydrochloric acid (38%). The aqueous solution of product was extracted three times with 250 parts of methylene chloride. The solution of product was dried with anhydrous sodium sulfate. The solvent was removed on a rotary evaporator at reduced pressure. The glassy residue was triturated with ether. 4.4 Parts of white solid with m.p. 183°-185° were obtained.

Workup

  1. temperatureheated to 80° for 30 hours
  2. temperatureAfter cooling the solution
  3. extractionThe aqueous solution of the product was then extracted three times with 250 parts of methylene chloride
  4. additionThe aqueous solution of the product was then acidified to pH 1 by addition at concentrated hydrochloric acid (38%)
  5. extractionThe aqueous solution of product was extracted three times with 250 parts of methylene chloride
  6. dry with materialThe solution of product was dried with anhydrous sodium sulfate
  7. customThe solvent was removed on a rotary evaporator at reduced pressure
  8. customThe glassy residue was triturated with ether
  9. custom4.4 Parts of white solid with m.p. 183°-185° were obtained

Sources & evidence

ORD record
ord-e0cf61e2614740338a2f4ba5dfbffc89
Source dataset
uspto-grants-1980_07
Patent number
US04213773

Reaction notes

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