Dimethylamine → N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

HRID 1045956Notes

Reaction equation

HRID 1045956 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[C:4]([C:10]([OH:12])=O)=[N:3]1.C1N=[CH:16][N:15](C(N2C=NC=C2)=O)[CH:14]=1.CNC>C1COCC1>[CH3:14][N:15]([CH3:16])[C:10]([C:4]1[C:5]([N+:7]([O-:9])=[O:8])=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:12]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 5359761-Methyl-4-nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 67076071N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 1-methyl-4-nitropyrazole-3-carboxylic acid (2.0 g) in THF (30 ml) was charged carbonyl-1,1′-diimidazole (1.9 g) over 1 hour at room temperature. The reaction was stirred overnight before cooling to 0° C. A solution of dimethylamine in THF (12 ml of a 2M solution) was added and the reaction stirred for 1 hour. The THF layer was separated and concentrated in vacuo. The crude product was purified by column chromatography on silica (30 g), eluting with 100% EtOAc (300 ml) to give N,N,1-trimethyl-4-nitropyrazole-3-carboxamide, 1235 mg.

Workup

  1. stirringthe reaction stirred for 1 hour
  2. customThe THF layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography on silica (30 g)
  5. washeluting with 100% EtOAc (300 ml)

Sources & evidence

ORD record
ord-fb9d8a624452451ca28cbe45e4ee5e15
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

Loading…