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Water → 4-Bromo-2-(methylsulfonamido)benzoic acid

HRID 1804069
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1804069
[NH2:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>O1CCCC1>[Br:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 17871390Methyl 2-Amino-4-bromobenzoate

Produkt 1

HCID 226210824-Bromo-2-(methylsulfonamido)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Methyl 2-amino-4-bromobenzoate (1 g) was dissolve in tetrahydrofuran (15 mL), triethylamine (4.2 mL) and methanesulfonyl chloride (0.74 mL) were added, and the mixture was stirred at room temperature for 6 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. After evaporation of the solvent, to the residue were added methanol (20 mL) and 1N aqueous sodium hydroxide solution (13 mL), and the mixture was stirred at 50-60° C. The mixture was acidified with 1N hydrochloric acid, and the precipitated solid was collected by filtration to give the title compound (0.964 g).

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. customAfter evaporation of the solvent
  3. additionto the residue were added methanol (20 mL) and 1N aqueous sodium hydroxide solution (13 mL)
  4. stirringthe mixture was stirred at 50-60° C
  5. filtrationthe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-61ac4a69d705430fa3275ad6cd34d92d
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354401B2

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