反応 #77823

反応方程式

(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

反応条件

後処理

1. 1
   その他A 2 l reaction flask
2. 2
   その他equipped
3. 3
   その他the internal reaction temperature below 30° C
4. 4
   workup.STIRRINGStirring
5. 5
   その他the reaction mixture was partitioned between water (1.0 l) and ethyl acetate (1.0 l)
6. 6
   その他After extensive mixing, the organic layer was separated
7. 7
   洗浄washed with a 5% aqueous solution of citric acid (500 ml), and saturated ammonium chloride (500 ml)
8. 8
   乾燥before drying with anhydrous sodium sulfate
9. 9
   その他Solvent was removed
10. 10
    その他the residual oil was evaporated once from acetonitrile
11. 11
    その他This product was sufficiently pure for further synthesis

実験手順

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%).

出典