Pyridine → HCID 13412531, Verbindung

HRID 2094786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2094786
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[Cl:10])[NH2:6].N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21].CCCCCC>ClCCl>[Cl:10][C:9]1[CH:8]=[CH:7][C:5]([NH:6][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:4][C:3]=1[C:2]([F:1])([F:11])[F:12]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8058HexaneHCID 15891Phenyl chloroformateHCID 675744-Chloro-3-(trifluoromethyl)aniline

Produkt 1

HCID 13412531HCID 13412531, VerbindungAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-trifluoromethyl-4-chloroaniline (55 g, 0.281 mol) and pyridine (56 ml, 0.7030 mol) were dissolved in dichloromethane (550 ml). The reaction mass was cooled to 0° C. to −5° C. and a solution of phenyl chloroformate (46 ml, 0.3515 mol) in dichloromethane (200 ml) was added drop wise maintaining the temperature of the reaction mass below 0° C. The reaction mass was stirred at 0° C. to 5° C. for 1-2 hours and quenched with water (250 ml) below 10° C. The organic phase was separated and washed with water followed by 1N HCl (100 ml). It was dried over sodium sulfate and concentrated to obtain solid. This solid was agitated with hexane (500 ml) at ambient temperature for 2-3 hours and filtered. The obtained product was then vacuum dried at 50° C. to give phenyl 4-chloro-3-(trifluoromethyl)phenylcarbamate (85 g) as white solid.

Aufarbeitung

  1. temperatureThe reaction mass was cooled to 0° C. to −5° C.
  2. temperaturewise maintaining the temperature of the reaction mass below 0° C
  3. customquenched with water (250 ml) below 10° C
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialIt was dried over sodium sulfate
  7. concentrationconcentrated
  8. customto obtain solid
  9. filtrationfiltered
  10. customvacuum dried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-08b28cc195c84b0ebaed32383d5be3c2
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445687B2

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