تفاعل #483023

معادلة التفاعل

4-(4-pyridyl)benzoic acid

thionyl chloride

2-amino-N-(4-methoxyphenyl)benzamide

→

brown solid

المردود 30.7%

2-[[4-(4-Pyridyl)benzoyl]amino]-N-(4-methoxyphenyl)benzamide Hydrochloride

المردود 30.7%

المذيبات

toluene

pyridine

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was heated to reflux
2. 2
   درجة الحرارةAfter 1 h the solution was cooled
3. 3
   أخرىthe solvent was removed in vacuo
4. 4
   أخرىthe residue was partitioned between ethyl acetate and water
5. 5
   أخرىThe organic phase was separated
6. 6
   غسيلwashed with sat. NaHCO3, brine
7. 7
   تجفيفdried (MgSO4)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated

الإجراء التجريبي

To a stirring suspension of 4-(4-pyridyl)benzoic acid (0.2 g, 1 mmol) in toluene (35 mL) was added thionyl chloride (0.55 mL, 7.5 mmol) and the mixture was heated to reflux. After 1 h the solution was cooled and added to a solution of 2-amino-N-(4-methoxyphenyl)benzamide (0.176 g, 0.73 mmol) in pyridine (2 mL) and toluene (5 mL). After stirring for 48 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was separated and washed with sat. NaHCO3, brine and dried (MgSO4), filtered and concentrated to give 103 mg of brown solid which was chromatographed by RPHPLC Method B. Upon standing, a sample of the title compound (14 mg, 4%) crystalized from one of the product containing fractions.

المصدر