Diethyl Ether → HCID 23442433, compound

HRID 2119654Notes

Reaction equation

HRID 2119654 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7](O)=[O:8].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[CH2:19](OCC)[CH3:20].[OH-].[Na+]>C(=O)([O-])[O-].[Na+].[Na+].[Cu]>[CH2:19]([N:11]1[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[C:7](=[O:8])[C:6]2[N:5]([CH3:10])[N:4]=[CH:3][C:2]1=2)[CH3:20]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7813p-ToluidineHCID 14798Sodium HydroxideHCID 6736874-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 23442433HCID 23442433, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid ((Y. A. Manaev et al., J. Gen. Chem. USSR. (Engl. Transl.), 1982, 52, 2291), 2.92 g, 11.6 mmol), p-toluidine (6.20 g, 57.9 mmol), and copper powder (1.17 g, 18.4 mmol) in 5% aqueous sodium carbonate (60 ml) was stirring at 100° C. for 5 h. After cooling to room temperature, diethyl ether (100 ml) and 2N aqueous sodium hydroxide (100 ml) were added. This mixture was filtered through a pad of Celite, which was washed with 2N sodium hydroxide (200 ml) and ether (100 ml). The separated aqueous layer was washed with ether (100 ml), filtered through a pad of Celite again, and acidified with concentrated hydrochloric acid. The precipitate was collected by filtration, and washed with water to give 1.77 g (76.6 mmol, 66%) of the title compound as a gray powder.

Workup

  1. filtrationThis mixture was filtered through a pad of Celite, which
  2. washwas washed with 2N sodium hydroxide (200 ml) and ether (100 ml)
  3. washThe separated aqueous layer was washed with ether (100 ml)
  4. filtrationfiltered through a pad of Celite again
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-ff080650d1d948edbbd7ca328b311fe0
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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