Ethanol, 1-ethoxy-2,2,2-trifluoro- → 4-chloro-N-(2,2,2-trifluoro-1-hydroxyethyl)benzamide

HRID 1358784

Reaktionsgleichung

Reaktionsgleichung von HRID 1358784
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C([O:13][CH:14](O)[C:15]([F:18])([F:17])[F:16])C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1>[OH:13][CH:14]([NH:8][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:15]([F:18])([F:17])[F:16]

Komponenten

5

Edukt 3

HCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 120844-ChlorobenzamideHCID 24436Sodium Sulfate

Produkt 1

HCID 113227584-chloro-N-(2,2,2-trifluoro-1-hydroxyethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 4-chlorobenzamide (22.0 g, 0.141 mol) and trifluoroacetaldehyde ethyl hemiacetal (25.0 g as is, 22.5 g real, 0.156 mol) in dioxane (200 mL) is treated with anhydrous sodium sulfate (10 g, to dry the 10% water in the hemiacetal) and refluxed for 60 hours. The solids are filtered and the filtrate is evaporated to a solid. The solids are dissolved in about 200 mL of 15% ethyl acetate in heptane. Unreacted starting material (5.6 g) crystallizes out and is filtered. The title product is obtained from the mother liquors as a white crystalline solid (22.1 g, 82.9% based on recovery of starting material): mp 139.5-140.5° C.; characterized by 1H and 19F NMR and Mass spectra. 1H NMR (DMSO-d6) δ9.45 (d, J=8.7 Hz, NH), 7.93, 7.54 (AB with fine splitting, J=8.4 Hz, ArH), 7.54 (broad s, OH), 5.90 (m, J=8.7, 2.9, 5.8 Hz, CH); 19F NMR δ−80.3 (d, J=5 Hz).

Aufarbeitung

  1. dry with materialto dry the 10% water in the hemiacetal) and
  2. temperaturerefluxed for 60 hours
  3. filtrationThe solids are filtered
  4. customthe filtrate is evaporated to a solid
  5. dissolutionThe solids are dissolved in about 200 mL of 15% ethyl acetate in heptane
  6. customcrystallizes out and
  7. filtrationis filtered

Quellen und Nachweise

ORD-Eintrag
ord-f28b91eb54054a85913918398751affb
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596902B2

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