Diethyl Ether → HCID 6618973, Verbindung

HRID 1886051

Reaktionsgleichung

Reaktionsgleichung von HRID 1886051
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[NH:4][CH2:5][CH2:6][OH:7].[CH3:12][N:13]=[C:14]=S.CI.CCOCC>CO>[OH:7][CH2:6][CH2:5][N:4]1[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=2[N:1]=[C:12]1[NH:13][CH3:14]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11167Methyl isothiocyanateHCID 21140322-((2-Aminophenyl)amino)ethan-1-ol

Produkt 1

HCID 6618973HCID 6618973, VerbindungAusbeute 21,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

According to the procedure of B. Agai, et al., Tetrahedron, 32, 839, (1976), to a cooled (0° C.), stirred suspension of 2-(2-aminoanilino)ethanol (30.4 g, 0.200 mol) in MeOH (100 mL) was added a solution of CH3NCS (14.6 g, 0.200 mol) in MeOH (60 mL) dropwise. The resulting mixture was stirred at room temperature for 4 hours and then heated under reflux for 15 minutes. CH3I (28.4 g, 0.200 mol) was added and the mixture was heated under reflux for 10 minutes, cooled to room temperature and stirred for 2 hours. Ether (200 mL) was added and the resulting precipitate was collected by filtration, taken up in nBuOH (140 mL), and heated under reflux for 10 hours. The mixture was cooled in the freezer for 3 hours and the white crystals were filtered. The material was dissolved in H2O and the solution was neutralized with 10% aqueous K 2 CO3. The white solid was collected by filtration to give 8.2 g (21%) of product m.p. >200° C.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature for 4 hours
  2. temperatureheated
  3. temperatureunder reflux for 15 minutes
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 10 minutes
  6. temperaturecooled to room temperature
  7. stirringstirred for 2 hours
  8. filtrationthe resulting precipitate was collected by filtration
  9. temperatureheated
  10. temperatureunder reflux for 10 hours
  11. temperatureThe mixture was cooled in the freezer for 3 hours
  12. filtrationthe white crystals were filtered
  13. dissolutionThe material was dissolved in H2O
  14. filtrationThe white solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-aa191f88c31d41e39f267e3acfdfff25
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149700

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