Hydrochloric Acid → HCID 15581955, Verbindung

HRID 1076369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1076369
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.C1([Li])C=CC=CC=1.[CH3:17][N:18]=[C:19]=[S:20].Cl>C1C=CC=CC=1.CCOCC.O.C1C=CC=CC=1>[CH3:1][O:2][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[C:19]([NH:18][CH3:17])=[S:20]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11167Methyl isothiocyanateHCID 2532202-(Methoxymethyl)pyridineHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 15581955HCID 15581955, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittelHCID 22174802Benzene etherLösungsmittel

Versuchsvorschrift

2-(Methoxymethyl)pyridine (4.4 g., 0.036 mole), dissolved in 25 ml. of dry benzene, is added dropwise to 20 ml. of 2M phenyl lithium (0.04 mole) in benzene/ether with cooling. The mixture is stirred for 30 minutes, then methyl isothiocyanate (2.6 g., 0.03 mole), dissolved in 40 ml. of dry benzene, is added dropwise with cooling. The resulting solution is stirred overnight. An equal volume of water is added and the solution is cooled and made acidic with 10% hydrochloric acid. The phases are separated, the organic phase is washed with water and the combined aqueous phases are made basic to about pH 9 then extracted with chloroform. The chloroform extracts are washed with water and dried over magnesium sulfate. Filtration and removal of solvent gives a residue which is recrystallized from isopropyl ether/ethanol to give 2-methoxy-N-methyl-2-(2-pyridyl)thioacetamide, m.p. 104°-105°C.

Aufarbeitung

  1. temperaturewith cooling
  2. stirringThe resulting solution is stirred overnight
  3. temperaturethe solution is cooled
  4. customThe phases are separated
  5. washthe organic phase is washed with water
  6. extractionthen extracted with chloroform
  7. washThe chloroform extracts are washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationFiltration and removal of solvent
  10. customgives a residue which
  11. customis recrystallized from isopropyl ether/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9b3e6539e2334cd1b4db8a3368c63ea0
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03956494

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