تفاعل #77823

معادلة التفاعل

(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

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر