Triethylamine → 2-[4-(3-Oxo-1,2-benzothiazol-2-yl)phenyl]acetic acid

HRID 611649

Reaktionsgleichung

Reaktionsgleichung von HRID 611649
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[S:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>CCOCCO>[O:24]=[C:23]1[C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[S:20][N:1]1[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 145334-Aminophenylacetic acidHCID 109107152-(Chlorothio)-benzoyl chloride

Produkt 1

HCID 4629372-[4-(3-Oxo-1,2-benzothiazol-2-yl)phenyl]acetic acidAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8076Glycol monoethyl etherLösungsmittel

Versuchsvorschrift

To a mixture of 7.55 g (0.05 mol) of 4-aminophenylacetic acid and 15.15 g (0.15 mol) of triethylamine in 25 mL of ethyl cellosolve was added 10.3 g (0.05 mol) of 2-chlorosulfenylbenzoyl chloride (Arzneimittel Forsch., 1964;14:1301). The mixture was stirred at room temperature for 3 hours, concentrated in vacuo, and water was added to the residue. The mixture was acidified with HCl and filtered to give 9.9 g of the title compound, mp 173-175° C.

Aufarbeitung

  1. concentrationconcentrated in vacuo, and water
  2. additionwas added to the residue
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-738a4c5d5278496bb9cb98d0d773692f
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06001863

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