Reacción #743464

Ecuación de reacción

hydrochloric acid

2-(2-thiomorpholin-4-ylethyl)isoindol-1,3-dione

4-t-butylbenzylisothiocyanate

hydrazine hydrate

→

4-t-butylbenzyl-3-(2-(thiomorpholin-4-yl)ethyl)thiourea

Disolventes

triethylamine

dimethylformamide

dichloromethane

methanol

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 3 hours
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   workup.ADDITIONTo the concentrate was added water (15 ml)
4. 4
   Filtraciónthe undissolved material was filtered off
5. 5
   ConcentraciónThe filtrate was concentrated
6. 6
   Otroto obtain
7. 7
   workup.STIRRINGby stirring at room temperature for 23 hours
8. 8
   Lavadowashed with water
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroThe residue was purified by column-chromatography (hexane/ethyl acetate=1/3) to the compound 15-3 (0.12 g) as a white solid

Procedimiento

2-(2-thiomorpholin-4-ylethyl)isoindol-1,3-dione 15-1 (2.76 g) was dissolved in a mixture of methanol (20 ml) and tetrahydrofuran (20 ml) and to the solution was added dropwise hydrazine hydrate (550 mg), followed by stirring for 21 hours. To the obtained solution was added 2 N aqueous hydrochloric acid solution (6 ml), and the mixture was stirred for 3 hours and then concentrated under reduced pressure. To the concentrate was added water (15 ml) and the undissolved material was filtered off. The filtrate was concentrated to obtain reaction mixture (1.62 g) as a solid. The obtained mixture (150 mg) was dissolved in dimethylformamide (5 ml) and to the solution was added 4-t-butylbenzylisothiocyanate (210 mg) and a small amount of triethylamine, followed by stirring at room temperature for 23 hours. The resulting mixture was diluted with dichloromethane, washed with water, and concentrated under reduced pressure. The residue was purified by column-chromatography (hexane/ethyl acetate=1/3) to the compound 15-3 (0.12 g) as a white solid.

Fuente