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

HRID 1754798Notes

Reaction equation

HRID 1754798 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
  2. temperatureto reflux 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-246b01c2b97c4ea3962bb2ed17c830c0
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

Loading…