4 Experimental Data
29
1.1g N,N-Dimethyl-4-phenylbutanamide
The product was prepared from 2.46 g (15 mmol) 4-phenylbutyric Acid and 7.5
mL (15 mmol) dimethylamine (2 M in THF) according to general procedure A.
Purification by column chromatography on silica gel (EtOAc:heptane = 2:1) afforded amide 1.1g in 71% (2.04 g) yield. All spectroscopic properties are in good
accordance with reported data.
[43]
Sulfonamides
Sulfonamides 1.2b,c,g were either generously donated by other members of our
group or received from commercial suppliers.
General procedure B for the synthesis of sulfonamides
To a solution of sulfonyl chloride (1 eq.) in THF (1 M) was added the primary
amine (3 eq.) or the primary amine hydrochloride salt (1 eq.) in combination with
triethylamine (2.5 eq.) at room temperature. The mixture was stirred for 16 h while
a precipitate formed. Then a solution of HCl (1 M) was added until a pH of 2 was
reached. The solution was extracted with EtOAc. The combined organic layers
were washed with a saturated solution of NaCl and dried over MgSO4. The solvent
was removed under reduced pressure which yielded the product. The crude product was used without further purification.
1.2a N-Methyl-4-nitrobenzenesulfonamide
The product was prepared from 2.22 g (10 mmol) 4-nitrobenzenesulfonyl chloride
and 15 mL (30 mmol) methylamine (2 M in THF) in 96% (2.12 g) yield according
to the general procedure B. All spectroscopic properties are in good accordance
with reported data.
[44]
29
1.1g N,N-Dimethyl-4-phenylbutanamide
The product was prepared from 2.46 g (15 mmol) 4-phenylbutyric Acid and 7.5
mL (15 mmol) dimethylamine (2 M in THF) according to general procedure A.
Purification by column chromatography on silica gel (EtOAc:heptane = 2:1) afforded amide 1.1g in 71% (2.04 g) yield. All spectroscopic properties are in good
accordance with reported data.
[43]
Sulfonamides
Sulfonamides 1.2b,c,g were either generously donated by other members of our
group or received from commercial suppliers.
General procedure B for the synthesis of sulfonamides
To a solution of sulfonyl chloride (1 eq.) in THF (1 M) was added the primary
amine (3 eq.) or the primary amine hydrochloride salt (1 eq.) in combination with
triethylamine (2.5 eq.) at room temperature. The mixture was stirred for 16 h while
a precipitate formed. Then a solution of HCl (1 M) was added until a pH of 2 was
reached. The solution was extracted with EtOAc. The combined organic layers
were washed with a saturated solution of NaCl and dried over MgSO4. The solvent
was removed under reduced pressure which yielded the product. The crude product was used without further purification.
1.2a N-Methyl-4-nitrobenzenesulfonamide
The product was prepared from 2.22 g (10 mmol) 4-nitrobenzenesulfonyl chloride
and 15 mL (30 mmol) methylamine (2 M in THF) in 96% (2.12 g) yield according
to the general procedure B. All spectroscopic properties are in good accordance
with reported data.
[44]