Dimethyl Sulfide → HCID 23359001, Verbindung

HRID 232646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 232646
[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[C:6]([F:11])=[CH:5][C:3]=1[NH2:4].[CH3:12][S:13][CH3:14].ClN1C(=O)CCC1=O.[OH-].[Na+]>C(N(CC)CC)C.ClCCl>[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[C:6]([F:11])=[C:5]([CH2:12][S:13][CH3:14])[C:3]=1[NH2:4]

Komponenten

7

Edukt 4

HCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 146512532,4,5-Trifluoro-3-methylaniline

Produkt 1

HCID 23359001HCID 23359001, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To anhydrous dichloromethane (170 ml) are added 2,4,5-trifluoro-3-methylaniline (16.89 g) and dimethyl sulfide (11 ml). Thereto N-chlorosuccinimide (17.2 g) is added gradually below 5° C. After stirring for 30 minutes, triethylamine (21 ml) is added dropwise and the mixture is refluxed over night. After the mixture is cooled and made alkaline with 5% aqueous sodium hydroxide solution, the resultant is extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (dichloromethane: n-hexane =1:1) to give 2,4,5-trifluoro-3-methyl-6-methylthiomethylaniline (8.3 g).

Aufarbeitung

  1. temperaturethe mixture is refluxed over night
  2. temperatureAfter the mixture is cooled
  3. extractionthe resultant is extracted with dichloromethane
  4. washthe extract is washed with water
  5. customdried
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe residue is purified by silica-gel column-chromatography (dichloromethane: n-hexane =1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3dde28863524422f8039c7a083abfc6b
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591744

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