Réaction #77823

Équation de réaction

(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

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source