تفاعل #1971523

معادلة التفاعل

3-hydroxy-2-butanone

2,4,6-trimethylaniline

malononitrile

→

off-white crystals

المردود 45.3%

2-amino-4,5-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrrole-3-carbonitrile

المردود 45.3%

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas refluxed
2. 2
   أخرىto remove water
3. 3
   درجة الحرارةthe mixture was refluxed for an additional 10 hours until all of the starting material
4. 4
   أخرىwas consumed
5. 5
   درجة الحرارةThe reaction mixture was cooled
6. 6
   أخرىprecipitate formed
7. 7
   ترشيحfiltered
8. 8
   غسيلThe solid was washed with a minimum amount of ethanol
9. 9
   workup.ADDITIONThe solid was diluted with 500 ml of benzene and product
10. 10
    workup.DISSOLUTIONwas dissolved
11. 11
    ترشيحwas filtered off
12. 12
    تركيزThe filtrate was concentrated
13. 13
    أخرىto give a tan solid which
14. 14
    أخرىwas recrystallized from ethanol

الإجراء التجريبي

A mixture of 3-hydroxy-2-butanone (100.000 g, 1.135 mol), 2,4,6-trimethylaniline (153.225 g, 1.135 mol) and p-toluenesulfonic acid (0.670 g) in 500 ml of benzene was refluxed using a Dean-Stark trap to remove water. After 2 hours, malononitrile (75.000 g, 1.135 mol) was added and the mixture was refluxed for an additional 10 hours until all of the starting material was consumed. The reaction mixture was cooled and precipitate formed and filtered. The solid was washed with a minimum amount of ethanol. The solid was diluted with 500 ml of benzene and product was dissolved. Some undesired product was insoluble and was filtered off. The filtrate was concentrated to give a tan solid which was recrystallized from ethanol to give 130.260 g of off-white crystals. 1H NMR (CDCl3) δ 1.68(s, 3H), 1.93(s, 6H), 2.05(s, 3H), 2.31(s, 3H), 3.62(brs, 2H), 6.95(s, 2H) ppm.

المصدر