Hydrochloric Acid → N-[2-(chloromethyl)-4-cyanophenyl]-2,2,2-trifluoroacetamide

HRID 388379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388379
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[C:5]([CH3:16])[CH:4]=1)#[N:2].S(Cl)([Cl:20])(=O)=O.Cl>C(Cl)(Cl)(Cl)Cl>[Cl:20][CH2:16][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=1[NH:9][C:10](=[O:15])[C:11]([F:13])([F:12])[F:14]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24648Sulfuryl chlorideHCID 58126830HCID 58126830, Verbindung2×

Produkt 1

HCID 86650575N-[2-(chloromethyl)-4-cyanophenyl]-2,2,2-trifluoroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

In a round-bottomed flask N-(4-cyano-2-methylphenyl)-2,2,2-trifluoroacetamide (Intermediate 1, 19.37 g, 85 mmol), sulfuryl dichloride (27.6 ml, 340 mmol) and diphenylperoxyanhydride (1.028 g, 4.24 mmol) were heated in carbon tetrachloride (210 ml) at 100° C. for 3 h. The mixture was cooled to room temperature and then the reaction mixture was poured into 2M HCl (350 mL). The organic layer was then collected and the solvent was removed to give N-[2-(chloromethyl)-4-cyanophenyl]-2,2,2-trifluoroacetamide as an orange oil, (25.54 g) which was used in the next step without further purification. This oil was added to triphenylphosphine (26.2 g, 100 mmol) and the mixture was heated in toluene (300 ml) at 110° C. for 3 h. The mixture was cooled to room temperature overnight and the precipitate was filtered and washed with small amounts of toluene and diethyl ether to give the title compound as an off-white solid (29.91 g);

Aufarbeitung

  1. customThe organic layer was then collected
  2. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-b5658a236c3c478fb3b9c7075fddf35a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377941B2

Notizen zur Reaktion

Wird geladen…