Water → 4-Chloro-N-[1-(4-chlorobutanoyl)-1H-pyrazol-3-yl]butanamide

HRID 32790

Reaction equation

HRID 32790 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.OP([O-])([O-])=O.[K+].[K+].[Cl:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19].[OH2:21]>C(Cl)Cl>[Cl:14][CH2:15][CH2:16][CH2:17][C:18]([NH:1][C:2]1[CH:6]=[CH:5][N:4]([C:18](=[O:21])[CH2:17][CH2:16][CH2:15][Cl:14])[N:3]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24450Potassium Phosphate, DibasicHCID 783704-Chlorobutyryl chlorideHCID 178418806HCID 178418806, compound

Product 1

HCID 597943554-Chloro-N-[1-(4-chlorobutanoyl)-1H-pyrazol-3-yl]butanamideYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-aminopyrazole (300 mg, 3.61 mmol) in anh. CH2Cl2 (6 mL), at r.t., under N2, was added K2HPO4 (1.26 g, 2 eq) and the reaction mixture was stirred at r.t. for 15 min. 4-Chloro-butyryl chloride (406 μL, 3.6 mmol) was then added and the reaction mixture was stirred for 24 hr. It was then poured into water and the phases were separated. The aqueous layer was extracted with EtOAc (2×20 mL) and the combined organic extracts were dried over anh. Na2SO4. The solids were filtered and the solvent evaporated. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 7:3) to give the title compound as a white solid (354 mg, 34%)

Workup

  1. stirringthe reaction mixture was stirred for 24 hr
  2. customthe phases were separated
  3. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  4. dry with materialthe combined organic extracts were dried over anh. Na2SO4
  5. filtrationThe solids were filtered
  6. customthe solvent evaporated
  7. customThe crude product was purified by flash chromatography (silica gel, cHex/EtOAc 7:3)

Sources & evidence

ORD record
ord-2154f7a9e0494f7ca847e5d03c3df2d0
Source dataset
uspto-grants-2008_09
Patent number
US07427630B2

Linked notes

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