Carbon Disulfide → Perhydrobenzimidazole-2-thione

HRID 583676

Reaktionsgleichung

Reaktionsgleichung von HRID 583676
[C:1](=[S:3])=S.[NH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[NH2:11]>C(Cl)Cl>[NH:4]1[C@H:5]2[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]2[NH:11][C:1]1=[S:3]

Komponenten

4

Edukt 2

HCID 6348Carbon DisulfideHCID 3429171,2-Diaminocyclohexane, cis-

Produkt 1

HCID 720914Perhydrobenzimidazole-2-thione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of carbon disulfide (1.1 mL, 17.9 mmol) and CH2Cl2 (10 mL) was treated dropwise with cis-1,2-diaminocyclohexane 20-1 (Aldrich) (2.0 g, 17.5 mmol) while maintaining the reaction mixture temperature below 20° C. with an ice bath. The reaction mixture was stirred at ambient temperature for 2.0 h after the addition was complete. Concentration followed by refluxing the resulting solid in H2O (20 mL) for 20 h gave a yellow solution. The cooled solution was extracted with CH2Cl2 and the CH2Cl2 portion was dried (MgSO4) and concentrated. The pale yellow solid was recrystallized from CH2Cl2 /ether to give 20-2 as a pale yellow solid. mp=164-166° C.

Aufarbeitung

  1. temperaturewhile maintaining the reaction mixture temperature below 20° C. with an ice bath
  2. additionafter the addition
  3. concentrationConcentration
  4. temperatureby refluxing the resulting solid in H2O (20 mL) for 20 h
  5. customgave a yellow solution
  6. extractionThe cooled solution was extracted with CH2Cl2
  7. dry with materialthe CH2Cl2 portion was dried (MgSO4)
  8. concentrationconcentrated
  9. customThe pale yellow solid was recrystallized from CH2Cl2 /ether

Quellen und Nachweise

ORD-Eintrag
ord-4ea14fb098a94fbfa362012e502f5820
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929120

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