Acetone → 5-azidocarbonyl-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1367430Notes

Reaction equation

HRID 1367430 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([OH:13])=O)[CH:6]=1)=[O:4].S(Cl)(Cl)=O.CC(C)=O.[N-:22]=[N+:23]=[N-:24].[Na+]>O>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([N:22]=[N+:23]=[N-:24])=[O:13])[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 180AcetoneHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 142660565-(Methoxycarbonyl)-1-Methyl-1H-Pyrazole-3-Carboxylic Acid

Product 1

HCID 576193625-azidocarbonyl-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Methyl-1H-pyrazole-3,5-dicarboxylic acid 5-methyl ester (641, 3.2 g, 17.0 mmol) was combined with thionyl chloride (5 mL). The reaction was heated to) reflux for 40 minutes and then concentrated twice from toluene. The resulting solid was dried under reduced pressure overnight. The product was dissolved into acetone (20 mL) and sodium azide (3.5 g, 54.0 mmol) was added in water (10 mL) rapidly at once. The obtained solution was stirred for one minute and then poured into ice-water (50 mL). The precipitate was filtered and dried under reduced pressure. The final compound was used without further purification (642, 2.8 g, 77%).

Workup

  1. temperatureThe reaction was heated to)
  2. temperaturereflux for 40 minutes
  3. concentrationconcentrated twice from toluene
  4. customThe resulting solid was dried under reduced pressure overnight
  5. filtrationThe precipitate was filtered
  6. customdried under reduced pressure
  7. customThe final compound was used without further purification (642, 2.8 g, 77%)

Sources & evidence

ORD record
ord-502844ec0a944b08ab7df15b97a75f28
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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