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

HRID 1376411

Reaction equation

HRID 1376411 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-03b639c79c4f4bd4a2742ffe81493c62
Source dataset
uspto-grants-1997_09
Patent number
US05663163

Linked notes

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