Water → 5-Amino-3-ethyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

HRID 411564

Reaktionsgleichung

Reaktionsgleichung von HRID 411564
[C:1]([C:3](=[C:7](OCC)[CH2:8][CH3:9])[C:4]([NH2:6])=[O:5])#[N:2].[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[C:15]=1[NH:22][NH2:23].O>CO>[NH2:2][C:1]1[N:22]([C:15]2[C:14]([Cl:13])=[CH:19][C:18]([Cl:20])=[CH:17][C:16]=2[Cl:21])[N:23]=[C:7]([CH2:8][CH3:9])[C:3]=1[C:4]([NH2:6])=[O:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 79234(2,4,6-Trichlorophenyl)hydrazineHCID 545251922-Cyano-3-ethoxypentenamide

Produkt 1

HCID 112560865-Amino-3-ethyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Part A: To a stirred solution of 320 mg (1.9 mmol) of 2-cyano-3-ethoxypentenamide in 7 mL of MeOH was added 465 mg (2.2 mmol) of 2,4,6-trichlorophenylhydrazine. The solution was stirred 3 h at reflux, treated with 2 mL of water, and allowed to stir an additional 1 h, cooling to RT. The white solid which precipitated was filtered, washed with 2:1 MeOH-water, and air-dried to afford 520 mg (82%) of 5-amino-3-ethyl-1-(2,4,6-trichlorophenyl) pyrazole-4-carboxamide, mp 186-188° C., Mass Spec(CI+): 331.9989(M)+.

Aufarbeitung

  1. temperatureat reflux
  2. stirringto stir an additional 1 h
  3. customThe white solid which precipitated
  4. filtrationwas filtered
  5. washwashed with 2:1 MeOH-water
  6. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-c2384bf51c5147008166b0a4bdc5b2d3
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559152B2

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