Sodium Iodide → {5-[(2-Chloro-5-nitro-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-methyl-amine

HRID 1726912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1726912
Cl.Cl[CH2:3][C:4]1[C:5]([NH:12][CH3:13])=[N:6][C:7]([S:10][CH3:11])=[N:8][CH:9]=1.[I-].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[NH2:26]>C(#N)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[NH:26][CH2:3][C:4]1[C:5]([NH:12][CH3:13])=[N:6][C:7]([S:10][CH3:11])=[N:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 226912-Chloro-5-nitroanilineHCID 21988143(5-Chloromethyl-2-methylsulfanyl-pyrimidin-4-yl)-methyl-amine hydrochloride

Produkt 1

HCID 68700288{5-[(2-Chloro-5-nitro-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-methyl-amineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

15.85 g (5-Chloromethyl-2-methylsulfanyl-pyrimidin-4-yl)-methyl-amine hydrochloride, 1.979 g sodium iodide, and 34.49 mL N—N-diisopropylethylamine were solved in 150 ml acetonitrile and cooled to 0° C. 17.085 g 2-Chloro-5-nitro-phenylamine dissolved in 150 ml acetonitrile were added slowly under stirring. The reaction mixture was stirred at room temperature for 48 hrs, then the solvent was evaporated. The residue was solved in a mixture of water/acetic acid ethyl ester (1:1), stirred and the crystalline product was isolated by filtration and dried for 48 h under vacuum at 40° C. The two phases of the mother liquor were separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, the solvent was evaporated and the residue was rubbed with diethyl ether. Both residues were combined and gave of the title product in 97% yield.

Aufarbeitung

  1. additionwere added slowly
  2. stirringThe reaction mixture was stirred at room temperature for 48 hrs
  3. customthe solvent was evaporated
  4. additionThe residue was solved in a mixture of water/acetic acid ethyl ester (1:1)
  5. stirringstirred
  6. customthe crystalline product was isolated by filtration
  7. customdried for 48 h under vacuum at 40° C
  8. customThe two phases of the mother liquor were separated
  9. extractionthe aqueous phase was extracted with dichloromethane
  10. dry with materialdried over sodium sulfate
  11. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c6e4527ee27f491b96e86471f678b9b3
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07494993B2

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