Dimethyl Sulfide → 2-Methylthiomethyl-3,4,6-trifluoroaniline

HRID 864326

Reaktionsgleichung

Reaktionsgleichung von HRID 864326
[F:1][C:2]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:3]=1[NH2:4].[CH3:11][S:12][CH3:13].ClN1C(=O)CCC1=O.[OH-].[Na+]>C(N(CC)CC)C.ClCCl>[CH3:11][S:12][CH2:13][C:5]1[C:6]([F:10])=[C:7]([F:9])[CH:8]=[C:2]([F:1])[C:3]=1[NH2:4]

Komponenten

7

Edukt 4

HCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 949532,4,5-Trifluoroaniline

Produkt 1

HCID 189744612-Methylthiomethyl-3,4,6-trifluoroaniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 2,4,5-trifluoroaniline (35.0 g) are added anhydrous dichloromethane (530 ml) and dimethyl sulfide (24.6 ml) and the mixture is cooled to 0° C. Thereto N-chlorosuccinimide (38.2 g) is gradually added below 5° C. After the mixture is stirred at the same temperature for 15 minutes, triethylamine (47.7 ml) is gradually added. After reflux for 12 hours, the resultant is made alkaline with 5% aqueous sodium hydroxide solution, extracted with dichloromethane, and the extract is dried over sodium sulfate and concentrated. The residue is purified with column chlomatography (silica-gel, dichloromethane: n-hexane=1: 4) to give 2-methylthiomethyl-3,4,6-trifluoroaniline (22.3 g).

Aufarbeitung

  1. customis gradually added below 5° C
  2. temperatureAfter reflux for 12 hours
  3. extractionextracted with dichloromethane
  4. dry with materialthe extract is dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified with column chlomatography (silica-gel, dichloromethane: n-hexane=1: 4)

Quellen und Nachweise

ORD-Eintrag
ord-c7c8453ffd6a405a93d4bd410e46506d
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563138

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