Carbon Disulfide → HCID 178505459, Verbindung

HRID 1696642

Reaktionsgleichung

Reaktionsgleichung von HRID 1696642
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([F:9])[C:3]=1[NH2:10].[C:11](=S)=[S:12]>C(O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:11]([SH:12])[NH:10][C:3]=2[C:4]=1[F:9]

Komponenten

4

Edukt 2

HCID 6348Carbon Disulfide3×HCID 27367533,4-Difluorobenzene-1,2-diamine

Produkt 1

HCID 178505459HCID 178505459, VerbindungAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1,2-diamino-3,4-difluoro-benzene (996 mg, 6.9 mmol) in 20 mL of ethanol in a 25 mL microwave tube, are added 2.0 mL (33.3 mmol) of carbon disulfide. The tube is capped and the reaction mixture is heated under microwaves at 120° C. twice for 20 minutes, upon which 1.0 mL (16.6 mmol) of carbon disulfide is added and heating under microwaves is pursued for 20 minutes. Carbon disulfide 2.0 mL (33.3 mmol) is added and heating is pursued for 30 minutes under microwaves at 150° C. The reaction mixture is then cooled to room temperature and concentrated to dryness under reduced pressure. The residue is dissolved into ethyl acetate and concentrated to dryness under reduced pressure. The residue is triturated into diisopropylether, filtered and washed once with diisopropylether. The solid is dried under reduced pressure. 0.35 g of 6,7-difluoro-1H-benzimidazole-2-thiol is obtained as mauve solid. LCMS-DAD-ELSD: 185(−): [M−H]−; 186(+): [M+H]+.

Aufarbeitung

  1. customThe tube is capped
  2. additionis added
  3. temperatureheating under microwaves
  4. temperatureheating
  5. waitis pursued for 30 minutes under microwaves at 150° C
  6. concentrationconcentrated to dryness under reduced pressure
  7. dissolutionThe residue is dissolved into ethyl acetate
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue is triturated into diisopropylether
  10. filtrationfiltered
  11. washwashed once with diisopropylether
  12. customThe solid is dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-63d3590e7827453595b7fc93b1982c04
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163768B2

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