2,5-diaminobenzene sulfonamide synthesis

15synthesis methods

Product Name:2,5-diaminobenzene sulfonamide
CAS Number:20896-44-0
Molecular formula:C6H9N3O2S
Molecular Weight:187.22

54734-85-9 Synthesis

54734-85-9
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20896-44-0
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Yield:20896-44-0 98%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in tetrahydrofuran;methanol at 23; under 2585.81 Torr;autoclave;Inert atmosphere;Industry scale;

Steps:

1.c

2-Amino-5-nitro-benzenesulfonamide (5.00 kg, 23.0 mol), methanol(65 L), tetrahydrofuran (65 L), and 10% palladium on carbon (250 g) were charged to an autoclave. The mixture was cycled with nitrogen and hydrogen purges (3 x), and the mixture was then stirred under hydrogen (50 psi) at 23 ⁰C overnight. The catalyst was removed by filtration and the filtrate was then concentrated in vacuo to give a brown solid. The solid was further dried in vacuo at 45 ⁰C to afford the desired product, 2,5-diamino-benzenesulfonamide (4.21 kg, 22.4 mol, 98%), as a solid. ¹H NMR (400 MHz, OMSO-d₆) δ: 4.54 (2H, bs), 4.98 (2H, bs), 6.55 - 6.60 (2H, m), 6.87 (IH, d, J= 2.2 Hz), 6.99 (2H, bs). LC-MS (ESI) calcd for C₆H₉N₃O₂S 187.04, found 188.3 [M+H⁺].

References:

WO2010/42834,2010,A1 Location in patent:Page/Page column 36-37