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

HRID 1838954Notes

Reaction equation

HRID 1838954 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+].[CH3:20][O:21][CH2:22][CH2:23]Br.C(Cl)Cl>C1COCC1.O>[CH2:1]([C:3]1[N:4]([CH2:23][CH2:22][O:21][CH3:20])[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 6344DichloromethaneHCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178438045HCID 178438045, compound

Product 1

HCID 112187175-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (2.5 kg, 13.6 Mol), sodium carbonate (1.8 Kg, 17.0 Mol) and 2-bromoethyl methyl ether (1.98 kg, 14.2 Mol) in THF (22.5 L) and water (2.5 L) was heated under reflux and stirred for 20 hours. The mixture was cooled to ambient temperature and CH2Cl2 (67.5 L) and water (22.5 L) were added. The resultant organic and aqueous layers were separated. The aqueous phase was extracted with CH2Cl2 (22.5 L) and the combined organic solution was distilled under atmospheric pressure and replaced with ethyl acetate (33 L) to a final volume of 17 L. The cooled mixture was granulated at ambient temperature for 2 hours, filtered and washed with ethyl acetate (2.5 L). This afforded 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide as a white crystalline solid, 2.10 kg, 57%. m.p.=140° C. Found: C, 44.46; H, 5.79; N, 23.01. C9H14N4O4 requires C, 44.63; H, 5.79; N, 23.14%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe resultant organic and aqueous layers were separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (22.5 L)
  5. distillationthe combined organic solution was distilled under atmospheric pressure
  6. waitThe cooled mixture was granulated at ambient temperature for 2 hours
  7. filtrationfiltered
  8. washwashed with ethyl acetate (2.5 L)

Sources & evidence

ORD record
ord-238c5669c86844fcb66eb8a16a5411b5
Source dataset
uspto-grants-2004_01
Patent number
US06677335B1

Reaction notes

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