Potassium Carbonate → 4-[2-(Dimethylamino)ethylthio]-benzoic acid

HRID 131282

Reaktionsgleichung

Reaktionsgleichung von HRID 131282
F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8]C(C)(C)C)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][SH:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][S:20][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 25798Captamine HydrochlorideHCID 2736444Tert-butyl 4-fluorobenzoate

Produkt 1

HCID 167872194-[2-(Dimethylamino)ethylthio]-benzoic acidAusbeute 110,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of tert-butyl 4-fluorobenzoate (300 mg), 2-(dimethylamino)-ethanethiol hydrochloride (420 mg), and potassium carbonate (620 mg) in dimethylsulfoxide (3.0 mL) is stirred at 80° C. for 4 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is concentrated in vacuo and to the residue is added 4N HCl-dioxane (1.5 mL). The mixture is stirred at room temperature overnight. The reaction mixture is diluted with ether and the precipitated crystals are collected by filtration to give 4-[2-(dimethylamino)ethylthio]-benzoic acid (380 mg, yield; 99%) as colorless crystals. MS (APCI) m/z; 226 [M+H]+

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. concentrationThe extract is concentrated in vacuo and to the residue
  3. additionis added 4N HCl-dioxane (1.5 mL)
  4. stirringThe mixture is stirred at room temperature overnight
  5. additionThe reaction mixture is diluted with ether
  6. filtrationthe precipitated crystals are collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a153716750a84def84a3a8d919f29795
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384952B2

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