2-(Ethoxymethylene)propanedinitrile → 5-amino-1-(2,3-dichlorophenyl)-1H-pyrazole-4-carbonitrile

HRID 1098235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098235
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:10][NH2:11].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C.ClC1C(Cl)=CC=CC=1NN>CO>[NH2:20][C:19]1[N:10]([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=2[Cl:2])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

Komponenten

5

Edukt 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 600691(2,3-Dichlorophenyl)hydrazineHCID 122765722,3-Dichlorophenylhydrazine HCl

Produkt 1

HCID 27972505-amino-1-(2,3-dichlorophenyl)-1H-pyrazole-4-carbonitrileAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(2,3-Dichlorophenyl)hydrazine hydrochloride (CAS no. 21938-47-6) (6.06 g, 28.4 mmol) was partitioned between EtOAc and 2M NaOH. Separated. The organic solution was dried (MgSO4), filtered and reduced to give the free base. 2-(Ethoxymethylene)malononitrile (3.47 g, 28.39 mmol) was added portionwise to a stirred solution of (2,3-dichlorophenyl)hydrazine in MeOH (50 mL), under nitrogen at 5° C. The resulting solution was allowed to stir for a further 1 hour. The reaction mixture was then heated to reflux and was stirred for 3 hours. The reaction mixture was allowed to cool to ambient temperature, then was evaporated to afford the product (7.19 g, 100%) which was used without further purification. 1H NMR (400 MHz, DMSO) δ 6.75 (2H, s), 7.48-7.53 (2H, m), 7.77 (1H, s), 7.79-7.84 (1H, m).

Aufarbeitung

  1. custom21938-47-6) (6.06 g, 28.4 mmol) was partitioned between EtOAc and 2M NaOH
  2. customSeparated
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. customto give the free base
  6. temperatureThe reaction mixture was then heated
  7. temperatureto reflux
  8. stirringwas stirred for 3 hours
  9. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5d164f5faced4fa98ede5f335c4876e9
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143263B2

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