Benzoyl chloride → 3,3-Dimethylcyclohexylthiourea

HRID 5030

Reaktionsgleichung

Reaktionsgleichung von HRID 5030
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[NH4+].[CH3:14][C:15]1([CH3:22])[CH2:20][CH2:19][CH2:18][CH:17]([NH2:21])[CH2:16]1>CC(C)=O>[CH3:14][C:15]1([CH3:22])[CH2:20][CH2:19][CH2:18][CH:17]([NH:21][C:11]([NH2:12])=[S:10])[CH2:16]1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 157537523,3-Dimethylcyclohexan-1-amine

Produkt 1

HCID 157537533,3-Dimethylcyclohexylthiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

59 g (0.42 mol) of benzoyl chloride were added dropwise over the course of 10 minutes to a solution of 33 g (0.44 mol) of ammonium thiocyanate in 100 ml of absolute acetone. The mixture was refluxed for 10 minutes and then 50.8 g (0.40 mol) of 3,3-dimethylcyclohexylamine were added dropwise, and the mixture was refluxed for a further 20 minutes and then stirred into 500 ml of ice-water. The precipitated solid was filtered off with suction, washed with water, dissolved in a hot mixture of 500 ml of 10% strength sodium hydroxide solution and 125 ml of ethanol and refluxed for 30 minutes. The reaction mixture was then diluted with ice-water, and the pH was initially adjusted to 1 with concentrated hydrochloric acid and then to 9 with solid sodium bicarbonate. The resulting precipitate was filtered off with suction, washed with water and dried at 80° C. under reduced pressure.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 10 minutes
  2. temperaturethe mixture was refluxed for a further 20 minutes
  3. filtrationThe precipitated solid was filtered off with suction
  4. washwashed with water
  5. dissolutiondissolved in a hot mixture of 500 ml of 10% strength sodium hydroxide solution and 125 ml of ethanol
  6. temperaturerefluxed for 30 minutes
  7. additionThe reaction mixture was then diluted with ice-water
  8. filtrationThe resulting precipitate was filtered off with suction
  9. washwashed with water
  10. customdried at 80° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f3c48c143b2340d1b98ea10ccaec69eb
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242948

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