Pyridine → 1-(2-Acetoxyethyl)-5-acetylaminopyrazole

HRID 248333

Reaction equation

HRID 248333 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([NH2:9])=[CH:7][CH:6]=[N:5]1.[C:10](OC(=O)C)(=[O:12])[CH3:11].N1[CH:22]=[CH:21]C=CC=1.C(=O)(O)[O-:24].[Na+]>[Cl-].[Na+].O.C(OCC)(=O)C>[C:10]([O:1][CH2:2][CH2:3][N:4]1[C:8]([NH:9][C:21](=[O:24])[CH3:22])=[CH:7][CH:6]=[N:5]1)(=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 3202812-(5-amino-1H-pyrazol-1-yl)ethan-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 229167651-(2-Acetoxyethyl)-5-acetylaminopyrazole

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

1-(2-Hydroxyethyl)-5-aminopyrazole (5 g) was added to acetic anhydride (14.7 ml) under stirring and ice-cooling, and pyridine (6.3 ml) was added thereto. The mixture was stirred for 2 hours at 25° C. The reaction mixture was added to a mixture of ethyl acetate (50 ml) and brine (50 ml). Then, the mixture was adjusted to pH 7.0 with an aqueous solution of sodium bicarbonate. The aqueous layer was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 1-(2-acetoxyethyl)-5-acetylaminopyrazole (5.98 g).

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was stirred for 2 hours at 25° C
  3. extractionThe aqueous layer was extracted with a mixture of ethyl acetate and tetrahydrofuran
  4. dry with materialThe extract was dried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-29387480911a4d3f8f2be171f1aacba3
Source dataset
uspto-grants-1993_05
Patent number
US05210080

Linked notes

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