M-Phenylenediamine → N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine

HRID 577397

Reaktionsgleichung

Reaktionsgleichung von HRID 577397
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[C:24]1([NH2:31])[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1>C(OCCO)C.C(OCC)(=O)C>[C:9]1([S:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:30][C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([NH2:31])[CH:25]=3)[N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 7935M-PhenylenediamineHCID 81531DiisopropylethylamineHCID 219952052-Chloro-4-(phenylthio)pyrimidine

Produkt 1

HCID 68746426N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8076Glycol monoethyl etherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2-chloro-4-(phenylthio)pyrimidine (300 mg, 1.35 mmol) and diisopropylethylamine (0.35 mL, 2.02 mmol) in 2-ethoxyethanol (2 mL), was added 1,3-phenylenediamine (291 mg, 2.70 mmol) in one portion. The whole was heated under reflux for 20 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), washed with water and brine. The organic solution was dried (Na2SO4), concentrated in vacuo. The residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (20:80→50:50) as eluant to give the product (167 mg, 42%).

Aufarbeitung

  1. temperatureThe whole was heated
  2. temperatureunder reflux for 20 hours
  3. washwashed with water and brine
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a2fff81be1694ddd90762a623013500b
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040549B2

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