Methanol → N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamine

HRID 1494644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494644
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([N:7]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=O.B.S(C)C.CO>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:7]([C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 6331BoraneHCID 150877884-chloro-N,N-bis(4-fluorophenyl)butanamide

Produkt 1

HCID 14722551N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamineAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred and cooled (0° C.) solution of 48 parts of 4-chloro-N,N-bis(4-fluorophenyl)butanamide in 108 parts of tetrahydrofuran were added 240 parts of a solution of borane, compound with thiobismethane, in tetrahydrofuran. After stirring overnight at room temperature, the reaction mixture was decomposed with 160 parts of methanol. After evaporation, The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and petroleum ether (20:80 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 32.5 parts (91.5%) of N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzeneamine as a residue (int. 70).

Aufarbeitung

  1. stirringAfter stirring overnight at room temperature
  2. customAfter evaporation
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and petroleum ether (20:80 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d2e5fc034c1d4792961653f083215c7d
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05026853

Notizen zur Reaktion

Wird geladen…