반응 #77823

반응 방정식

(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

반응 조건

후처리

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

실험 절차

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%).

출처