Phosphorus oxychloride → 2,4-Difluoro-1-(isocyano(tosyl)methyl)benzene

HRID 1929964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929964
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[NH:10][CH:11]=O.P(Cl)(Cl)(Cl)=O>COCCOC>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N+:10]#[C-:11])[S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:14])=[O:15]

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 22236872N-((2,4-Difluorophenyl)(tosyl)methyl)formamide

Produkt 1

HCID 222368732,4-Difluoro-1-(isocyano(tosyl)methyl)benzeneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a solution of N-((2,4-difluorophenyl)(tosyl)methyl)formamide (7.31 g, 22.5 mmol) in DME (100 mL) at about −10° C. was added phosphorus oxychloride (Fluka, 6.28 mL, 67.4 mmol) followed by dropwise addition of TEA (15.7 mL, 112 mmol) in DME (10 mL). The reaction mixture was stirred at about −5° C. for about 3 h. The reaction mixture was poured into ice-cold water (250 mL) and extracted with EtOAc (3×50 mL). The organic layer was dried with MgSO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography using heptane/EtOAc (gradient; 1:0 to 1:1) to give the title compound (1.38 g, 20.0%), as a yellow solid. LC/MS (Table 1, Method a) Rt=2.96 min; MS m/z: 306.1 (M−H)−.

Aufarbeitung

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f050ee4f28a04737b163935a093fc02d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188083B2

Notizen zur Reaktion

Wird geladen…