تفاعل #161035

معادلة التفاعل

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

2-benzothiophenecarboxylic acid

1-aminocyclohexanecarboxylic acid phenylmethyl ester

1-hydroxybenzotriazole

→

title compound

المردود 91.0%

1-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester

المردود 91.0%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةUnder ice-cooling
2. 2
   workup.DISTILLATIONthe reaction solvent was distilled off under reduced pressure
3. 3
   workup.ADDITIONWater was added to the residue
4. 4
   استخلاصthe mixture was extracted with ethyl acetate twice
5. 5
   غسيلThe obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution
6. 6
   تجفيفa saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure, diethyl ether
8. 8
   workup.ADDITIONwas added to the obtained residue
9. 9
   workup.STIRRINGthe mixture was stirred overnight
10. 10
    ترشيحThe crystal was collected by filtration
11. 11
    أخرىheated/dried under reduced pressure

الإجراء التجريبي

Under ice-cooling, 5.9 g (31 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 5 g (28 mmol) of 2-benzothiophenecarboxylic acid, 6.5 g (28 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester and 4.5 g (29 mmol) of 1-hydroxybenzotriazole in methylene chloride. After the mixture was stirred at room temperature overnight, the reaction solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate twice. The obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, diethyl ether was added to the obtained residue, and the mixture was stirred overnight. The crystal was collected by filtration and heated/dried under reduced pressure to obtain 10 g (91%) of the title compound.

المصدر