Hydrochloric Acid → HCID 19369056, compound

HRID 848953Notes

Reaction equation

HRID 848953 reaction equation
[Cl:1][C:2]1([CH3:39])[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]1[N:9]1[C:13](=[O:14])[CH2:12][C:11]([NH:15][C:16]2[CH:17]=[C:18]([CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:20])=[N:10]1.[C:40](OC(=O)C)(=[O:42])[CH3:41].[OH-].[Na+].Cl>C(Cl)(=O)C.CO>[Cl:1][C:2]1([CH3:39])[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]1[N:9]1[C:13](=[O:14])[CH2:12][C:11]([N:15]([C:16]2[CH:17]=[C:18]([CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:20])[C:40](=[O:42])[CH3:41])=[N:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 178443283HCID 178443283, compound

Product 1

HCID 19369056HCID 19369056, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6367Acetyl chlorideSolvent

Procedure

Dodecyl 3-{N-[1-(2-chloro-2,4-dimethylphenyl)-4,5-dihydro-5-oxo-1H-pyrazol-3-yl]-amino}-4-methoxy-benzoate (10.5 g, 18.9 mmol) was dissolved in acetyl chloride (50 ml) and acetic anhydride (35 ml) and the solution was heated under reflux for 1.5 hrs. The solution was cooled, then it was slowly poured into ice/water (750 ml) and the resulting sticky solid was extracted with ethyl acetate (2×100 ml). The combined extracts were dried (MgSO4) and evaporated to give an oil. Sodium hydroxide (0.8 g, 18.9 mmol) was added to a solution of the oil in methanol (80 ml) and the mixture was stirred at room temperature for 4 hrs. The solution was poured slowly into 3N hydrochloric acid (500 ml), the aqueous liquor was decanted off and the residue was dissolved in ethyl acetate (100 ml). The organic solution was dried (MgSO4) and evaporated to give a glass. The crude material was recrystallized from methanol (50 ml) to give pure product as a white solid, 5.8 g, 51%.

Workup

  1. temperatureunder reflux for 1.5 hrs
  2. temperatureThe solution was cooled
  3. extractionthe resulting sticky solid was extracted with ethyl acetate (2×100 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customto give an oil
  7. customthe aqueous liquor was decanted off
  8. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  9. dry with materialThe organic solution was dried (MgSO4)
  10. customevaporated
  11. customto give a glass
  12. customThe crude material was recrystallized from methanol (50 ml)
  13. customto give pure product as a white solid, 5.8 g, 51%

Sources & evidence

ORD record
ord-e08e28b969ff417eadd2ff6bc1d110a0
Source dataset
uspto-grants-2000_01
Patent number
US06010837

Reaction notes

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