Cesium carbonate → Methyl 4-(N-(4-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate

HRID 658606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658606
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][S:9]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>CC(C)=O>[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][N:8]([CH2:7][C:6]2[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)(=[O:11])=[O:10])=[CH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 26527056Methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate

Produkt 1

HCID 57422334Methyl 4-(N-(4-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoateAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate (Example 5-10b) (4.3 g, 12.8 mmol) was dissolved in acetone (70 mL). Cesium carbonate (8.57 g, 25.6 mmol) and (4-fluorobenzyl bromide (1.76 mL, 14.08 mmol) were added and the mixture was stirred at room temperature overnight. The inorganic salts were filtered off and acetone was removed in vacuo. The residue was re-dissolved in ethyl acetate, washed with water and brine, then the organic layer was dried over magnesium sulfate and concentrated. The crude product was purified by re-crystallization with ethyl acetate/hexanes to afford pure Methyl 4-(N-(4-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate (3.7 g, 65%) as a white solid. 1H NMR (400 MHz, CDCl3): δ, ppm: 3.77 (s, 3H), 3.98 (s, 3H), 4.27 (s, 2H), 4.28 (s, 2H), 6.74 (d, 2H, J=8 Hz), 6.92 (m, 4H), 7.03 (m, 2H), 7.88 (d, 2H J=8 Hz), 8.16 (d, 2H, J=8 Hz).

Aufarbeitung

  1. filtrationThe inorganic salts were filtered off
  2. customacetone was removed in vacuo
  3. dissolutionThe residue was re-dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by re-crystallization with ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9585903bad894615b0c064ae5b09095a
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076491B2

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