반응 #483023

반응 방정식

4-(4-pyridyl)benzoic acid

thionyl chloride

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

→

brown solid

수율 30.7%

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

수율 30.7%

용매

toluene

pyridine

toluene

반응 조건

후처리

1. 1
   온도the mixture was heated to reflux
2. 2
   온도After 1 h the solution was cooled
3. 3
   기타the solvent was removed in vacuo
4. 4
   기타the residue was partitioned between ethyl acetate and water
5. 5
   기타The organic phase was separated
6. 6
   세척washed with sat. NaHCO3, brine
7. 7
   건조dried (MgSO4)
8. 8
   여과filtered
9. 9
   농축concentrated

실험 절차

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.

출처