1-Chloro-2,4-Dinitrobenzene → 2-(2,4-Dinitrophenylthio)ethanol

HRID 1823212

Reaktionsgleichung

Reaktionsgleichung von HRID 1823212
[F-].[K+].[N+:3]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1Cl)([O-:5])=[O:4].[SH:16][CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:3]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[S:16][CH2:17][CH2:18][OH:19])([O-:5])=[O:4]

Komponenten

6

Edukt 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 522689Potassium Fluoride

Produkt 1

HCID 92127792-(2,4-Dinitrophenylthio)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

217 parts of potassium fluoride are introduced into a solution of 500 parts of 2,4-dinitro-1-chlorobenzene in 590 parts of N,N-dimethylformamide (DMF) and the reaction mixture is stirred for 5 hours at room temperature. 350 parts of 2-mercaptoethanol are then added dropwise, whereupon the internal temperature rises to from 60 to 65° C., and stirring is then carried out for about 15 hours at that temperature. Then, any starting materials still present are made to react by adding 34 parts of potassium carbonate. Finally, the mixture is left to cool to room temperature, salts are filtered off and the filtrate is concentrated. The oily crude product is discharged onto water, whereupon a yellow crystalline precipitate separates out. After filtering off under suction, washing and drying, 2-[2,4-dinitrophenylsulfanyl]ethanol is obtained in an almost quantitative yield and high purity.

Aufarbeitung

  1. customrises to from 60 to 65° C.
  2. stirringstirring
  3. waitis then carried out for about 15 hours at that temperature
  4. customto react
  5. waitFinally, the mixture is left
  6. temperatureto cool to room temperature
  7. filtrationsalts are filtered off
  8. concentrationthe filtrate is concentrated
  9. filtrationAfter filtering off under suction
  10. washwashing
  11. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-dd982d2c7c574d2c893625c10d8252f6
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07038024B2

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