Toluene → HCID 86653327, compound

HRID 509962Notes

Reaction equation

HRID 509962 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:8]=[C:7]([C:19]([OH:21])=O)[CH:6]=1)=[O:4].C1(C)C=CC=CC=1.S(Cl)(Cl)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>O>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:8]=[C:7]([C:19]([N:33]=[N+:34]=[N-:35])=[O:21])[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 58259152HCID 58259152, compound

Product 1

HCID 86653327HCID 86653327, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a round bottom flask, 1-(4-methoxy-benzyl)-1H-pyrazole-3,5-dicarboxylic acid 5-methyl ester (105, 5.48 g, 18.9 mmol) was combined with 20 mL of toluene and thionyl chloride (6 mL, 80 mmol). The reaction was heated at reflux for 40 minutes, then concentrated 2× from toluene and the resulting solid dried under vacuum. This was dissolved in 30.0 mL of acetone and sodium azide (3.8 g, 58 mmol) in 10.0 mL of water was added and stirred for 1 minute. The reaction was poured into 250 mL of ice water and stirred slowly. The resulting precipitate was collected by filtration and dried under vacuum to provide the desired compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 40 minutes
  3. concentrationconcentrated 2× from toluene
  4. customthe resulting solid dried under vacuum
  5. dissolutionThis was dissolved in 30.0 mL of acetone
  6. stirringstirred slowly
  7. filtrationThe resulting precipitate was collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-6fd9b5ea3e2b47a1bcf24fefbdfa3e10
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

Loading…