Dimethylformamide → HCID 178440443, compound

HRID 855595Notes

Reaction equation

HRID 855595 reaction equation
[CH:1]([C:4]1[C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:9](O)=[O:10])[NH:7][N:8]=1)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.C[N:22](C)C=O>ClCCl>[CH:1]([C:4]1[C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:9]([NH2:22])=[O:10])[NH:7][N:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178440445HCID 178440445, compound

Product 1

HCID 178440443HCID 178440443, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-isopropyl-4-nitro-2H-pyrazole-3-carboxylic acid (Farmaco, 46, 11, 1991, 1337-1350) (6 g, 0.03 mol) in N,N-dimethylformamide (69 μL) and dichloromethane (67 mL) was cooled to −5° C. in ice/acetone. Oxalyl chloride (11.48 g, 0.09 mol) was added over 30 minutes and the reaction mixture stirred for 1 hour, the reaction mixture was then allowed to return to room temperature for 2 hours. The reaction mixture was concentrated in vacuo and remaining solvent azeotroped with dichloromethane. The resulting solid was suspended in tetrahydrofuran (70 mL), cooled to 0° C. and 0.880 ammonia (25 mL) added. The reaction mixture was stirred for 30 minutes and then concentrated in vacuo. The resulting solid was suspended in water, filtered and dried at 70° C. under vacuum to yield the product.

Workup

  1. waitto return to room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customazeotroped with dichloromethane
  4. addition0.880 ammonia (25 mL) added
  5. stirringThe reaction mixture was stirred for 30 minutes
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered
  8. customdried at 70° C. under vacuum
  9. customto yield the product

Sources & evidence

ORD record
ord-403f6f4d11a44dd39ec19a3a1b9b98c7
Source dataset
uspto-grants-2007_08
Patent number
US07262192B2

Reaction notes

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