反应详情

A mixture consisting of 5.0 grams of 2-methylthiobenz(cd)indol-2-amine hydriodide, 2.8 grams of 7-(1H-imidazol-1-yl)heptylamine, and 75 ml of ethanol as stirred and heated under reflux for 16 hours. After addition of 20 ml of 1N NaOH solution, the reaction mixture was taken to dryness in vacuo. The residue was partitioned between 150 ml of dichloromethane and 100 ml of water. A solid appeared at the interface. It was collected by filtration, added to the dichloromethane filtrate, and the mixture taken to dryness in vacuo. The residual orange oil was dissolved in 100 ml of acetone and added to a stirred boiling solution of 3.5 grams of fumaric acid in 800 ml of acetone. The resultant yellow precipitate was collected, washed with acetone, and dissolved in 200 ml of hot water. The solution was clarified by treatment with activated charcoal. The clear aqueous solution was cooled and made basic with 0.5 N NaOH solution. The resultant orange precipitate was collected, washed with water and dried in vacuo at room temperature. The yield of the title compound was 2.2 grams, and the mp was 48° C.-50° C.

1. temperatureheated
2. temperatureunder reflux for 16 hours
3. customThe residue was partitioned between 150 ml of dichloromethane and 100 ml of water
4. filtrationIt was collected by filtration
5. additionadded to the dichloromethane filtrate
6. dissolutionThe residual orange oil was dissolved in 100 ml of acetone
7. additionadded to a stirred
8. customThe resultant yellow precipitate was collected
9. washwashed with acetone
10. dissolutiondissolved in 200 ml of hot water
11. temperatureThe clear aqueous solution was cooled
12. customThe resultant orange precipitate was collected
13. washwashed with water
14. customdried in vacuo at room temperature