Thionyl Chloride → Ska-31

HRID 1382708

Reaktionsgleichung

Reaktionsgleichung von HRID 1382708
S(Cl)(Cl)=O.[C:5]1([NH:15][C:16]([NH2:18])=[S:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1>C(OCC)(=O)C>[N:15]1[C:5]2[C:14]3[C:9]([CH:8]=[CH:7][C:6]=2[S:17][C:16]=1[NH2:18])=[CH:10][CH:11]=[CH:12][CH:13]=3

Komponenten

4

Edukt 2

HCID 24386Thionyl Chloride2×HCID 7363661-(1-Naphthyl)-2-thiourea

Produkt 1

HCID 94880Ska-31Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 160 ml thionyl chloride 64.0 g (0.32 mol) of 1-(1-naphthyl)-2-thiourea was added portionwise while the temperature of the reaction mixture was kept at 30°-40° (internal temperature). After the addition was completed, an additional 80 ml of thionyl chloride was added and the mixture was heated at 50°-55° for 4 hours. It was cooled to room temperature and diluted with 400 ml of ethyl acetate and filtered. The filtrate in 400 ml of water was basified with concentrated ammonium hydroxide and the aqueous suspension was extracted with ethyl acetate (3×200 ml). The combined ethyl acetate solutions were dried (MgSO4) and the solvent was removed under reduced pressure to give 46.6 g (74%) of naphtho[1,2-d]thiazol-2-amine, mp 186°-188°.

Aufarbeitung

  1. customwas kept at 30°-40°
  2. additionAfter the addition
  3. temperaturethe mixture was heated at 50°-55° for 4 hours
  4. filtrationfiltered
  5. extractionthe aqueous suspension was extracted with ethyl acetate (3×200 ml)
  6. dry with materialThe combined ethyl acetate solutions were dried (MgSO4)
  7. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a8cb38c03b64bcd85de0f54e3e82f3c
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808580

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