Chlorosuccinimide → 5-Chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamine

HRID 52775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52775
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[N:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:18]N1C(=O)CCC1=O.CCOC(C)=O.C1CCCCC1>CC#N>[Cl:18][C:10]1[C:11]([NH2:15])=[CH:12][N:13]=[N:14][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=1

Komponenten

5

Edukt 3

HCID 31398ChlorosuccinimideHCID 199596756-[3-(Trifluoromethyl)phenyl]-4-pyridazinamineHCID 21867204Cyclohexane ethylacetate

Produkt 1

HCID 199596635-Chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamineAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

6-[3-(Trifluoromethyl)phenyl]-4-pyridazinamine (2.0 g, 0.0084 mole, Compound No. 4) and N-chlorosuccinimide (0.61 g, 0.004 mole) were refluxed under N2 in CH3CN (50 mL) for 1.5 h. After this time no starting material was present by TLC. The mixture was partitioned between EtOAc/water. The organic layer was extracted again with water, dried (MgSO4), filtered and evaporated to give a crude oil. The oil was chromatographed on a Prep-500 using EtOAc/cyclohexane (9:1) to give a crude solid. The solid was recrystal-lized from EtOAc/cyclohexane to give 5-chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamine (0.57 g, 50% yield, Compound No. 35) as a tan solid.

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc/water
  2. extractionThe organic layer was extracted again with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a crude oil
  7. customThe oil was chromatographed on a Prep-500 using EtOAc/cyclohexane (9:1)
  8. customto give a crude solid

Quellen und Nachweise

ORD-Eintrag
ord-d052b4381e5c4c09a46e158086914306
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616789

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