Sodium Chloride → CID 86697018

HRID 588598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588598
[N:1]([O-])=O.[Na+].[CH]Cl.[C:7]1([C:13]2[C:17]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:16]([NH2:26])[NH:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Na+].[Cl-:28]>C(Cl)Cl>[Cl:28][C:18]1[C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:1][N:26]=[C:16]2[NH:15][N:14]=[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:17]=12

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 6432229CID 6432229HCID 23668193Sodium NitriteHCID 178509104HCID 178509104, Verbindung

Produkt 1

HCID 86697018CID 86697018Ausbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium nitrite (2.88 g, 42 mmol) was added portionwise to cHCl (314 mL) at −15° C. and stirred for 15 min. 3-phenyl-4-(2-phenylethynyl)-1H-pyrazol-5-amine (5.4 g, 21 mmol) was added as a solid, followed by the addition of CH2Cl2 (10 mL). The reaction mixture was allowed to warm up and stirred at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 (44 mL) and NaCl (2.7 g) was added. The reaction mixture was heated to 50° C. for 1 d. The layers were separated and the organic layer was washed with water, dried (phase separator cartridge) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, iso-hexanes/ethyl acetate 4:1, then CH2Cl2/ethyl acetate 1:0 to 4:1) yielding the title compound as a solid (3.0 g).

Aufarbeitung

  1. temperatureto warm up
  2. stirringstirred at room temperature for 1 h
  3. additionwas added
  4. customThe layers were separated
  5. washthe organic layer was washed with water
  6. customdried (phase separator cartridge)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, iso-hexanes/ethyl acetate 4:1

Quellen und Nachweise

ORD-Eintrag
ord-b815a9652b30464fb5a2d3e5dccadb75
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227976B2

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