Hydrochloric Acid → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acid

HRID 2265198

Reaktionsgleichung

Reaktionsgleichung von HRID 2265198
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][S:13]([C:16]1[C:21]2=[N:22][S:23][N:24]=[C:20]2[CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].O[Li].O.Cl>C1COCC1.O>[N:24]1[S:23][N:22]=[C:21]2[C:16]([S:13]([NH:12][C:5]3[CH:6]=[C:7]([Cl:11])[C:8]([Cl:10])=[CH:9][C:4]=3[C:3]([OH:25])=[O:2])(=[O:15])=[O:14])=[CH:17][CH:18]=[CH:19][C:20]=12

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 687705432-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoic acid methyl ester

Produkt 1

HCID 160907562-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoic acid methyl ester (0.95 g, 2.3 mmol) in THF (21 mL) and water (7 mL) was added LiOH.H2O (0.38 g, 9.1 mmol). The biphasic mixture was stirred overnight at rt. The mixture was acidified with conc. HCl and extracted with DCM (3×). The combined organic layers were dried (MgSO4) and concentrated to provide 0.80 g (88%) of the pure acid as a white solid. 1H NMR (500 MHz, CDCl3): 11.07 (s, 1H), 8.41 (dd, J=7.0, 1.0, 1H), 8.27 (dd, J=8.8, 1.0, 1H), 8.01 (s, 1H), 7.94 (s, 1H), 7.75 (dd, J=8.8, 7.0, 1H).

Aufarbeitung

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-421a8e52c3784cd28667d3504dcade89
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855292B2

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