1,3-Dichloro-2-isocyanatobenzene → HCID 57710265, Verbindung

HRID 1038697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038697
[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH3:17])[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[N:27]=[C:28]=[O:29]>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[NH:27][C:28](=[O:29])[N:16]([C:14]1[CH:15]=[C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:1])[CH3:18])[CH:4]=2)[N:11]=[CH:12][N:13]=1)[CH3:17]

Komponenten

4

Edukt 2

HCID 6045371,3-Dichloro-2-isocyanatobenzene2×HCID 66670065HCID 66670065, Verbindung

Produkt 1

HCID 57710265HCID 57710265, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of N-(3-dimethylamino-phenyl)-N′-methyl-pyrimidine-4,6-diamine (243.3 mg, 1 mmol), 2,6-dichlorophenyl isocyanate (188 mg, 1 mmol) in dry dimethylformamide (2.5 mL) is shaken for 14 h at 90° C. Two additional portions (188 mg, 1 mmol each) of 2,6-dichlorophenyl isocyanate are added after 14 h and 26 h. After 38 h the reaction mixture is evaporated in vacuo and the residue is distributed between ethyl acetate and half-saturated K2CO3 solution. The organic layer is dried over Na2SO4, evaporated, and the residue purified by flash chromatography (hexane/ethyl acetate). The combined pure fractions are evaporated, the residue triturated with CH2Cl2 and the solid filtered off and dried in vacuo to afford the title compound.

Aufarbeitung

  1. customAfter 38 h the reaction mixture is evaporated in vacuo
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customevaporated
  4. customthe residue purified by flash chromatography (hexane/ethyl acetate)
  5. customThe combined pure fractions are evaporated
  6. customthe residue triturated with CH2Cl2
  7. filtrationthe solid filtered off
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a051174cb3594565b1c1c74ff41a554b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552002B2

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