Reacción #7000

Ecuación de reacción

sulfonyl chloride

pyridine

2,4-dinitrobenzenesulfonyl chloride

TFA

→

2,4-dinitrobenzenesulfonamide

Disolventes

THF

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe solution was concentrated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
3. 3
   Filtraciónfiltered through a pad of solid K2CO3
4. 4
   ConcentraciónThe filtrate was concentrated in vacuo
5. 5
   Otroto give the corresponding crude amine
6. 6
   workup.ADDITIONwas then added
7. 7
   workup.WAITAfter a further 4 h
8. 8
   Otrohad been consumed
9. 9
   workup.ADDITIONThe reaction mixture was diluted with Et2O
10. 10
    Lavadowashed with 1N aq HCl, saturated aq NaHCO3 and brine
11. 11
    Secadodried (MgSO4)
12. 12
    Filtraciónfiltered
13. 13
    Concentraciónconcentrated in vacuo

Procedimiento

A solution of Part A compound (1.01 g, 2.37 mmol) and TFA (8 mL) in CH2Cl2 (30 mL) was stirred at RT for 4.5 h. The solution was concentrated in vacuo, and the residue was dissolved in CH2Cl2 and filtered through a pad of solid K2CO3. The filtrate was concentrated in vacuo to give the corresponding crude amine. To a solution of the crude amine in THF (11.9 mL) were added pyridine (0.383 mL, 4.74 mmol) and 2,4-dinitrobenzenesulfonyl chloride (0.85 g, 3.19 mmol) and the solution was stirred at RT for 15 h. Since some starting material still remained at this point, more sulfonyl chloride (0.32 g, 1.2 mmol) was then added. After a further 4 h, HPLC analysis indicated that all starting material had been consumed. The reaction mixture was diluted with Et2O, washed with 1N aq HCl, saturated aq NaHCO3 and brine, dried (MgSO4), filtered and concentrated in vacuo to provide the crude 2,4-dinitrobenzenesulfonamide

Fuente