Hydrochloric Acid → HCID 70294282, compound

HRID 848954Notes

Reaction equation

HRID 848954 reaction equation
N[C:2]1[NH:3][N:4]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[C:5](=[O:7])[CH:6]=1.[C:17](Cl)(=[O:20])[CH2:18][CH3:19].Cl.[OH-].[K+].[N:25]1C=CC=CC=1>O1CCCC1.CO.C(O)(=O)C>[O:7]=[C:5]1[N:4]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[N:3]=[C:2]([CH:18]([CH3:19])[C:17]([NH2:25])=[O:20])[CH2:6]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14797Potassium HydroxideHCID 62324Propionyl chlorideHCID 972955-Amino-2-(2,4,6-trichloro-phenyl)-1,2-dihydro-pyrazol-3-one

Product 1

HCID 70294282HCID 70294282, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Amino-1-(2,4,6-trichlorophenyl)-5-pyrazolone (35.0 g, 125 mmole) was dissolved in dry tetrahydrofuran (350 ml) and pyridine (35 ml) and the solution was cooled in an ice-bath to 10° C. A solution of propionyl chloride (35.15 g, 0.18 mmole) in tetrahydrofuran (60 ml) was added dropwise keeping the temperature below 10° C. The mixture was stirred at room temperature for 48 hrs then it was poured into dilute hydrochloric acid (2.51). The resulting gum was extracted with ethyl acetate (700 ml) and the solution was washed with water and dried (MgSO4). Evaporation of the solvent under reduced pressure gave a light brown oil which was dissolved in methanol (120 ml). A solution of potassium hydroxide (70.0 g, 125 mmol) in methanol was added dropwise with stirring and the mixture was stirred for 0.5 hrs. Glacial acetic acid was added to the suspension and stirred for 2 hr. The buff colored solid was filtered off, washed with water and dried in a vacuum oven. The yield of product was 35.54 g, 85%.

Workup

  1. customthe temperature below 10° C
  2. extractionThe resulting gum was extracted with ethyl acetate (700 ml)
  3. washthe solution was washed with water
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent under reduced pressure
  6. customgave a light brown oil which
  7. stirringwith stirring
  8. stirringthe mixture was stirred for 0.5 hrs
  9. stirringstirred for 2 hr
  10. filtrationThe buff colored solid was filtered off
  11. washwashed with water
  12. customdried in a vacuum oven

Sources & evidence

ORD record
ord-ac9545b137a54c0a8e6b9619a7a8e0ed
Source dataset
uspto-grants-2000_01
Patent number
US06010837

Reaction notes

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