Benzenesulfonamide, 3-(hydroxymethyl)- (9CI) synthesis
- Product Name:Benzenesulfonamide, 3-(hydroxymethyl)- (9CI)
- CAS Number:220798-42-5
- Molecular formula:C7H9NO3S
- Molecular Weight:187.22
636-76-0
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220798-42-5
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Yield:220798-42-5 90%
Reaction Conditions:
with borane-THF in tetrahydrofuran at 0 - 20; for 4 h;Inert atmosphere;
Steps:
3-(Hydroxymethyl)benzenesulfonamide, S6[5]
37 mL of 1 M Borane-THF-complex solution (37.3 mmol, 3.0 eq) were added dropwise to 0 °C cold solution of 2.50 g of 3-sulfamoylbenzoic acid, S5, (12.4 mmol 1.0 eq) in 20 mL of abs. tetrahydrofuran under argon. After stirring for 2 hours at room temperature additional 15 mL of borane-THF-complex solution was added and the mixture was stirred for 2 hours at room temperature. The reaction suspension was cool to 0 °C and quenched with 45 mL of methanol. 100 mL of 2 M hydrochloric acid were added after 15 min. Methanol was removed under reduced pressure and the aqueous residue was extracted with ethyl acetate (3 x 150 mL). The combine organic phases were washed twice with brine (100 mL), dried over Na2SO4, filtered and the solvent was removedin vacuum to yield 2.10 g (90%) of a yellow oil.
References:
Lill, Andreas P.;R?dl, Carmen B.;Steinhilber, Dieter;Stark, Holger;Hofmann, Bettina [European Journal of Medicinal Chemistry,2015,vol. 89,p. 503 - 523] Location in patent:supporting information
59777-67-2
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56593-99-8
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4025-64-3
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65-85-0
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