N-[4-[(4-cyanophenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]-N'-(1-methylethyl)urea → 4-[[4-[(2,6-Dichlorophenyl)methyl]-6-(methylamino)-1,3,5-triazin-2-yl]amino]benzonitrile

HRID 25048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25048
NC(NC)NC(=O)CC1C(Cl)=CC=CC=1Cl.[C:17]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]2[N:31]=[C:30]([CH2:32][C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:40])[N:29]=[C:28]([NH:41][C:42](NC(C)C)=O)[N:27]=2)=[CH:21][CH:20]=1)#[N:18]>CN(C=O)C>[Cl:39][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:40])[C:33]=1[CH2:32][C:30]1[N:29]=[C:28]([NH:41][CH3:42])[N:27]=[C:26]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:17]#[N:18])=[CH:24][CH:23]=2)[N:31]=1

Komponenten

4

Edukt 2

HCID 22281695N-[4-[(4-cyanophenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]-N'-(1-methylethyl)ureaHCID 22281696N-[amino(methylamino)methyl]-2,6-dichloro-benzeneacetamide

Produkt 1

HCID 4864244-[[4-[(2,6-Dichlorophenyl)methyl]-6-(methylamino)-1,3,5-triazin-2-yl]amino]benzonitrileAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
104 °C

Versuchsvorschrift

A mixture of N-[amino(methylamino)methyl]-2,6-dichloro-benzeneacetamide (4.15 g) and intermediate 6 (3.05 g) in DMF (25 ml) was stirred and refluxed for 20 hours. The solvent was evaporated, the residue dissolved in DMF (25 ml) and heated at 80° C. for 16 hours and at 100-108° C. for another 66 hours. The reaction mixture was cooled, quenched with water, extracted with diethyl ether, and washed with dilute NaOH, water, brine, and dried over K2CO3. The solvent was evaporated, and the residue was purified by flash column chromatography, and recrystallized from 2-propanol, and finally from methanol, yielding 0.78 g (12.6%) of 4-[[4-[(2,6-dichlorophenyl)methyl]-6-(methyl-amino)-1,3,5-triazin-2-yl]amino]benzonitrile (compound 7, mp. 229-230° C.).

Aufarbeitung

  1. temperaturerefluxed for 20 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in DMF (25 ml)
  4. temperatureThe reaction mixture was cooled
  5. customquenched with water
  6. extractionextracted with diethyl ether
  7. washwashed with dilute NaOH, water, brine
  8. dry with materialdried over K2CO3
  9. customThe solvent was evaporated
  10. customthe residue was purified by flash column chromatography
  11. customrecrystallized from 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-e467c01eec8c42ff8dc5e12caf09ba09
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858609B2

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