Ethyl Acetoacetate → HCID 178437907, compound

HRID 636414Notes

Reaction equation

HRID 636414 reaction equation
[C:1]1([S:7]([C:10]2[C:14]([CH2:15][CH3:16])=[N:13][NH:12][C:11]=2[NH2:17])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](OCC)(=[O:23])[CH2:19][C:20]([CH3:22])=O>C(O)(=O)C>[C:1]1([S:7]([C:10]2[C:14]([CH2:15][CH3:16])=[N:13][N:12]3[C:18]([OH:23])=[CH:19][C:20]([CH3:22])=[N:17][C:11]=23)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 178438051HCID 178438051, compound

Product 1

HCID 178437907HCID 178437907, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.9 g (11.5 mmol) of 4-benzenesulphonyl-5-ethyl-2H-pyrazol-3-ylamine and 1.8 ml (13.8 mmol) of ethyl acetoacetate in 10 ml of acetic acid was heated at reflux for 3 hrs. The reaction solution was cooled to RT and evaporated. The residue was partitioned between CH2Cl2 and H2O and the aqueous phase was washed three times with 150 ml of CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. Crystallization from ethyl acetate yielded 2.6 g (71%) of 3-benzenesulphonyl-2-ethyl-5-methyl-pyrazolo[1,5-a]pyrimidin-7-ol as colorless crystals.

Workup

  1. temperatureat reflux for 3 hrs
  2. customevaporated
  3. customThe residue was partitioned between CH2Cl2 and H2O
  4. washthe aqueous phase was washed three times with 150 ml of CH2Cl2
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-4dbb740a32af46f793d0f1322dbf4805
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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