Isopropanol → HCID 67214738, Verbindung

HRID 2420792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2420792
[NH2:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.[C:12]1([CH3:26])[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:13]=1[CH:20]=[C:21]([C:24]#[N:25])[C:22]#[N:23].C(O)(C)C>N1C=CC=CC=1>[NH2:25][C:24]1[N:3]2[N:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]2[N:1]=[C:20]([C:13]2[C:12]([CH3:26])=[CH:17][C:16]([CH3:18])=[CH:15][C:14]=2[CH3:19])[C:21]=1[C:22]#[N:23]

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 5930572-[(2,4,6-Trimethylphenyl)methylene]propanedinitrile2×HCID 178469928HCID 178469928, Verbindung

Produkt 1

HCID 67214738HCID 67214738, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 155 mg (1 mmol) of 3-amino-4-carbethoxypyrazole and 196 mg (1 mmol) of (mesitylmethylene)malononitrile (Intermediate 3) in 3 mL of anhydrous pyridine was stirred at reflux under air for 3 days and then cooled and concentrated in vacuo. Because LC-MS indicated the presence of considerable dihydro intermediate, 112 mg (0.49 mmol) of 2,3-dichloro-5,6-cyano-1,4-benzoquinone (DDQ) and 3 mL of isopropanol were added to the residue, and the mixture was stirred at ambient temperature for 1 h. The mixture was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (elution with 2% methanol in dichloromethane) to give the title compound as an orange solid. LC-MS 350 (M+1).

Aufarbeitung

  1. temperatureat reflux under air for 3 days
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. additionwere added to the residue
  5. concentrationThe mixture was concentrated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel (elution with 2% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-6bcfea483b7845eea928544d81b5a7c9
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956061B2

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