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