Water → HCID 67170430, compound

HRID 872890Notes

Reaction equation

HRID 872890 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].[Cl:13][O-].[Na+].O>C(O)(=O)C>[C:1]([C:4]1[C:8]([Cl:13])=[C:7]([C:9]([O:11][CH3:12])=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 16767345Methyl 3-acetyl-1H-pyrazole-5-carboxylateHCID 23665760Sodium Hypochlorite2×

Product 1

HCID 67170430HCID 67170430, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a flask containing methyl 3-acetyl-1H-pyrazole-5-carboxylate (4.0 g, 0.0238 mol) in acetic acid (60 ml), 5% sodium hypochlorite (284 ml, 0.190 mol) was added dropwise at 10-12° C. The mixture was stirred at RT over three nights adding more 5% sodium hypochlorite (177 ml, 0.119 mol in total) during the second and third day. Water was added to the reaction mixture and the product was extracted with ethyl acetate. Organic layer was dried with anhydrous Na2SO4 and concentrated. The crude product was recrystallized twice from n-hexane. Yield 23%. LC-MS: [M+1]=203.5.

Workup

  1. additionwas added dropwise at 10-12° C
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialOrganic layer was dried with anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was recrystallized twice from n-hexane

Sources & evidence

ORD record
ord-e6448e4f571f48f695d7b6d470e21a63
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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