Sodium Hydroxide → [2-(4-Bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid

HRID 2229562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229562
C([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([CH3:14])=[CH:9][C:8]=1[C:15](=[S:26])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[F:25])C.[OH-].[Na+]>C(O)C>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:15]([C:8]2[CH:9]=[C:10]([CH3:14])[C:11]([F:13])=[CH:12][C:7]=2[O:6][CH2:5][C:4]([OH:27])=[O:3])=[S:26])=[C:19]([F:25])[CH:20]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22093484[2-(4-Bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid ethyl ester

Produkt 1

HCID 22093458[2-(4-Bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acidAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirring solution of [2-(4-bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid ethyl ester (0.79 g, 1.53 mmol) in ethanol (7.6 mL, 0.2 M) and treated with aqueous NaOH (2 N, 7.4 mL, 9.15 mmol) in an analogous fashion to Example 45, Step 9 to provide [2-(4-bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid (0.65 g, 98%) as a yellow solid: mp 162-164° C.; Rf 0.41 (20% methanol in methylene chloride); 1H NMR (DMSO-d6, 300 mHz) δ 10.64 (t, J=5.0 Hz, 1H), 7.61 (d, J=9.0 Hz, 1H), 7.52 (dd, J1=9.6 Hz, J2=1.7 Hz, 1H), 7.45-7.36 (m, 2H), 7.00 (d, J=11.4 Hz, 1H), 4.89 (bd d, J=5.1 Hz, 2H), 4.78 (s, 2H), 2.15 (d, J=1.2 Hz, 3H); ESI-LC/MS m/z calcd for C17H14BrF2NO3S: 428.98; found 428.0 (M−1)−; Anal. calcd for C17H14BrF2NO3S: C, 47.45; H, 3.28; N, 3.26; S, 7.45. Found C, 47.54; H, 3.19; N, 3.11; S, 7.33.

Quellen und Nachweise

ORD-Eintrag
ord-16dd1f9a0e74469693349a622605bbac
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420426B1

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