Ammonia → 6-Phenylhexane-1-thiol

HRID 618630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618630
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.NC(N)=[S:16].N.Cl>C(O)C>[C:8]1([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][SH:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 561788(6-Bromohexyl)benzeneHCID 2723790Thiourea

Produkt 1

HCID 104880806-Phenylhexane-1-thiol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

15.0 g (62.2 mmol) 1-bromo-6-phenyl-hexane (described in the unexamined laid-open patent application of the int. Appl. PCT/EP95/04413) dissolved in 40 ml ethanol was added under a nitrogen atmosphere to a solution of 7.10 g (93.3 mmol) thiourea in 30 ml ethanol. After boiling for 7 hours at reflux temperature, it was allowed to cool to room temperature, admixed with 33 ml concentrated ammonia and heated for 4 h to reflux. Subsequently it was acidified to pH 1 with 15 ml concentrated HCl. It was extracted three times with 200 ml ether each time, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and the solvent was removed in a vacuum. The residue was taken up in dichloromethane, the solid was suction filled, rewashed with dichloromethane and the filtrate was evaporated in a vaccum. 9.80 g (82%) 13 as a colourless oil.

Aufarbeitung

  1. temperatureat reflux temperature, it
  2. temperatureheated for 4 h
  3. temperatureto reflux
  4. extractionIt was extracted three times with 200 ml ether each time
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed in a vacuum
  8. additionfilled
  9. customthe filtrate was evaporated in a vaccum

Quellen und Nachweise

ORD-Eintrag
ord-5e0175bef9144212bb074ab704820e6a
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05955452

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