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

HRID 131282

Reaction equation

HRID 131282 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 167872194-[2-(Dimethylamino)ethylthio]-benzoic acidYield 110.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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]+

Workup

  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

Sources & evidence

ORD record
ord-a153716750a84def84a3a8d919f29795
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Linked notes

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