Sodium Iodide → 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

HRID 2187119Notes

Reaction equation

HRID 2187119 reaction equation
[CH2:1]([C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([C:11]([NH2:13])=[O:12])[NH:5][N:4]=1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[CH3:22][O:23][CH2:24][CH2:25]Br>CC(CC)=O.O>[CH2:1]([C:3]1[N:4]([CH2:25][CH2:24][O:23][CH3:22])[N:5]=[C:6]([C:11]([NH2:13])=[O:12])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178438045HCID 178438045, compound

Product 1

HCID 112187175-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamideYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (25 g, 0.136 Mol), sodium carbonate (18 g, 0.17 Mol) and sodium iodide (20.4 g, 0.136 Mol) were suspended in ethyl methyl ketone (125 mL) at room temperature. 2-bromoethyl methyl ether (12.8 mL, 0.142 Mol) was added and the mixture was heated to reflux and stirred for 70 hours. The mixture was cooled to ambient temperature and water (250 mL) was added. The resultant slurry was warmed to reflux and held at that temperature for 30 min before cooling to room temperature. The resultant precipitate was granulated at room temperature for 3 h, filtered and vacuum dried to afford 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide as a yellow crystalline solid 24.3 g, 74%. Data as reported for Example (g)(i).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureThe resultant slurry was warmed
  4. temperatureto reflux
  5. waitheld at that temperature for 30 min
  6. temperaturebefore cooling to room temperature
  7. filtrationfiltered
  8. customvacuum dried

Sources & evidence

ORD record
ord-207336dc03b249259a1599871271702c
Source dataset
uspto-grants-2002_06
Patent number
US06407259B1

Reaction notes

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