تفاعل #7831

معادلة التفاعل

Thionyl chloride

3,5-dimethoxy-4-methylbenzoic acid

2-aminophenol

diisopropylethyl amine

→

3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling
2. 2
   أخرىreaction mixture to rt
3. 3
   تركيزconcentrated mixture in vacuo
4. 4
   تركيزAfter concentrating mixture in vacuo
5. 5
   أخرىthe resulting brown oil was purified by flash chromatography on silica gel
6. 6
   غسيلa gradient elution from 1:9 EtOAc

الإجراء التجريبي

Thionyl chloride (10 mL) and 3,5-dimethoxy-4-methylbenzoic acid (1.0 g, 5.1 mmol) was refluxed under argon until no starting material was observed by TLC. After cooling reaction mixture to rt, concentrated mixture in vacuo. The resulting brown oil was added to a mixture of 2-aminophenol (580 mg, 5.3 mmol), diisopropylethyl amine (1.1 mL, 6.3 mmol) and THF (40 mL) at 0° C. and then brought to rt overnight. After concentrating mixture in vacuo, the resulting brown oil was purified by flash chromatography on silica gel, using a gradient elution from 1:9 EtOAc:hexanes to 1:1 EtOAc:hexanes. This afforded the desired intermediate, 3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide, as a colorless solid.

المصدر