Reaktion #77823

Reaktionsgleichung

(S)-1-(4-chlorophenyl)ethylamine

N-chloro-carbamoyl-4-[(4-cyclohexylphenylamino)methyl]benzoic acid methyl ester

triethylamine

NMP

→

4-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl ester

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 2 l reaction flask
2. 2
   Sonstigeequipped
3. 3
   Sonstigethe internal reaction temperature below 30° C
4. 4
   workup.STIRRINGStirring
5. 5
   Sonstigethe reaction mixture was partitioned between water (1.0 l) and ethyl acetate (1.0 l)
6. 6
   SonstigeAfter extensive mixing, the organic layer was separated
7. 7
   Waschenwashed with a 5% aqueous solution of citric acid (500 ml), and saturated ammonium chloride (500 ml)
8. 8
   Trocknenbefore drying with anhydrous sodium sulfate
9. 9
   SonstigeSolvent was removed
10. 10
    Sonstigethe residual oil was evaporated once from acetonitrile
11. 11
    SonstigeThis product was sufficiently pure for further synthesis

Vorschrift

A 2 l reaction flask equipped with mechanical stirring was charged with N-chloro-carbamoyl-4-[(4-cyclohexylphenylamino)methyl]benzoic acid methyl ester (94 g, 0.244 mol), NMP (1.0 l) and triethylamine (68 ml, 0.487 mol). To the clear solution was added drop wise (S)-1-(4-chlorophenyl)ethylamine (38.0 g, 0.244 mol), keeping the internal reaction temperature below 30° C. Stirring was continued for 2 hours, then the reaction mixture was partitioned between water (1.0 l) and ethyl acetate (1.0 l). After extensive mixing, the organic layer was separated, and washed with a 5% aqueous solution of citric acid (500 ml), and saturated ammonium chloride (500 ml), before drying with anhydrous sodium sulfate. Solvent was removed, and the residual oil was evaporated once from acetonitrile. This product was sufficiently pure for further synthesis. Yield: 103 g (84%).

Quelle