ChemicalBook CAS DataBase List 2-NITROPHENOL-4-SULFOMETHYL AMIDE

2-NITROPHENOL-4-SULFOMETHYL AMIDE synthesis

4synthesis methods

Product Name:2-NITROPHENOL-4-SULFOMETHYL AMIDE
CAS Number:96-58-2
Molecular formula:C7H8N2O5S
Molecular Weight:232.21

Benzenesulfonyl chloride, 4-hydroxy-3-nitro- (9CI)

147682-51-7
35 suppliers
inquiry

74-89-5 Synthesis

74-89-5
7 suppliers
$13.44/25ML

96-58-2
14 suppliers
inquiry

Yield:96-58-2 42%

Reaction Conditions:

with dmap in tetrahydrofuran at 20;

Steps:

1

PREPARATION 73-amino-4-hydroxy-//-methylbenzenesulfonamideStep 1 . 4-hydroxy-/V-methyl-3-nitrobenzenesulfonamideA suspension of 4-hydroxy-3-nitrobenzenesulfonyl chloride (0.749 g, 3.15 mmol) and DMAP (0.077 g, 0.630 mmol) in THF (7.880 mL) was treated with CH₃NH₂ (2 M in THF, 6.30 mL, 12.61 mmol). The resulting mixture was then stirred at rt overnight. The mixture was then filtered and the filtrate partitioned between CH₂CI₂ and satd. aq. NaHC0₃. The layers were separated by hydrophobic frit. The aq. layer was then extracted at pH 7, pH 5 (twice), and pH 2. The pH 5 and pH 2 extracts were then combined and concentrated to afford 4-hydroxy-/V-methyl-3-nitrobenzenesulfonamide (0.31 1 g, 42%) as a pale yellow solid. ¹ H NMR (400 MHz, DMSO-d₆) δ 12.09 (br. s., 1 H), 8.22 (d, J = 2.52 Hz, 1 H), 7.88 (dd, J = 2.27, 8.81 Hz, 1 H), 7.53 (q, J = 4.95 Hz, 1 H), 7.31 (d, J = 8.81 Hz, 1 H), 2.42 (d, J = 5.04 Hz, 3H); MS (m/z) 232.8 (M+H)⁺.

References:

WO2011/88027,2011,A1 Location in patent:Page/Page column 60