تفاعل #939049

معادلة التفاعل

triethylamine

Oxalyl chloride

3-cyano-4-isobutyloxybenzoic acid

hydrochloric acid

methyl 3 amino-2-chlorobenzoate

→

Methyl 2-chloro-3-(3-cyano-4-isobutyloxybenzoylamino)benzoate

المذيبات

THF

dichloromethane

DMF

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder cooling with ice
2. 2
   درجة الحرارةheated
3. 3
   درجة الحرارةunder reflux for 3 hours
4. 4
   workup.DISTILLATIONto distill the solvent off
5. 5
   workup.ADDITIONToluene was added to the residue
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   workup.ADDITIONTHF (10 mL) was added to the residue
8. 8
   workup.STIRRINGThe resulting mixture was stirred for 14 hours at room temperature
9. 9
   غسيلwashed with aqueous 1M hydrochloric acid and aqueous saturated sodium hydrogen carbonate
10. 10
    تجفيفdried over anhydrous magnesium sulfate
11. 11
    workup.DISTILLATIONto distill the solvent off

الإجراء التجريبي

Oxalyl chloride (889 mg, 7.0 mmol) was dropwise added to a solution of 3-cyano-4-isobutyloxybenzoic acid (767 mg, 3.5 mmol) in dichloromethane (10 mL) under cooling with ice. Subsequently, a catalytic amount of DMF was added. The mixture was then stirred for one hour at room temperature, heated under reflux for 3 hours, and placed under reduced pressure to distill the solvent off. Toluene was added to the residue and the solvent was distilled off under reduced pressure. THF (10 mL) was added to the residue. Further, a solution of methyl 3 amino-2-chlorobenzoate (497 mg, 2.68 mmol) and triethylamine (1.39 mL, 10 mmol) in THF (10 mL). The resulting mixture was stirred for 14 hours at room temperature, and toluene and aqueous 1M hydrochloric acid were added. The organic portion was taken out, washed with aqueous 1M hydrochloric acid and aqueous saturated sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and placed under reduced pressure to distill the solvent off.

المصدر