Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178482518, Verbindung

HRID 1075047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1075047
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[C:2]([NH2:4])=[NH:3].C1(N)C(F)=C(F)C(F)=[C:17]([NH2:24])C=1F.Cl.Cl.CO[C:31]1[C:35](OC)=[N:34][S:33](=[O:39])(=[O:38])[N:32]=1>CO>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:31]2[C:35]([NH:24][CH3:17])=[N:34][S:33](=[O:39])(=[O:38])[N:32]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Komponenten

5

Edukt 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxideHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Produkt 1

HCID 178482518HCID 178482518, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 4.27 g; 14.0 mmoles) in 30 ml of methanol was added to a well stirred suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.50 g; 14.0 mmoles) in 250 ml of methanol at 10°. After 15 minutes at 10°, the solution was cooled to 1° in a cooling bath and anhydrous methylamine was bubbled into the solution for 10 minutes. The reaction mixture was evaporated under reduced pressure and the residue placed on 60 g of silica gel and chromatographed using a gradient elution of methylene chloride-methanol. The appropriate fraction containing 4.53 g of product was placed on 80 g of aluminum oxide and rechromatographed using a gradient elution of ethyl acetate-methanol. The appropriate fractions were combined and evaporated to give a foam which crystallized from methanol to yield (2.38 g) of the title compound, mp 196°-198° (dec).

Aufarbeitung

  1. temperaturethe solution was cooled to 1° in a cooling bath
  2. customanhydrous methylamine was bubbled into the solution for 10 minutes
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customchromatographed
  5. washa gradient elution of methylene chloride-methanol
  6. additionThe appropriate fraction containing 4.53 g of product
  7. customrechromatographed
  8. washa gradient elution of ethyl acetate-methanol
  9. customevaporated
  10. customto give a foam which
  11. customcrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ddec9101c9ce4152a9fb3008d1558aee
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04394508

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