Phosgeniminium chloride → HCID 73852578, Verbindung

HRID 1864147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1864147
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[CH3:19][N+:20]([CH3:24])=[C:21](Cl)[Cl:22].[Cl-]>ClCCCl>[Cl:22][C:21]([N:20]([CH3:24])[CH3:19])=[N:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18]

Komponenten

4

Edukt 2

HCID 2723945Phosgeniminium chlorideHCID 217925045-Amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazole-4-carbonitrile

Produkt 1

HCID 73852578HCID 73852578, VerbindungAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of 5-amino-1-(4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile (1.2 g, 4.57 mmol) and phosgeniminium chloride (0.900 g, 7.08 mmol) in dry 1,2-dichloroethane was refluxed for 4 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (30 to 50% ethyl acetate/hexanes) to yield 1-chloro-N′-[4-cyano-2-(4-methanesulfonyl-phenyl)-2H-pyrazol-3-yl]-N,N-dimethyl-formamidine (1.3 g, 80%) as a yellowish solid. Exact mass calculated for C14H14ClN5O2S 351.06, found 352.20 (MH+, 100%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (30 to 50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7c27b459d6794cb7adc1f8390b9ee836
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625906B2

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