4-Aminobenzyl alcohol → Pyridine-2-sulfonic acid (4-hydroxymethyl-phenyl)-amide

HRID 970937Notes

Reaction equation

HRID 970937 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26]>>[OH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)(=[O:27])=[O:26])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 693314-Aminobenzyl alcoholHCID 81531DiisopropylethylamineHCID 3787675Pyridine-2-sulfonyl Chloride

Product 1

HCID 85814308Pyridine-2-sulfonic acid (4-hydroxymethyl-phenyl)-amideYield 47%

Procedure

Reaction of (4-Amino-phenyl)-methanol (249 mg, 2.03 mmol), N,N-diisopropylethylamine (294 uL, 1.69 mmol), and pyridine-2-sulfonyl chloride (300 mg, 1.69 mmol) for 1 h at room temperature followed by column chromatography on silica gel (CH2Cl2/MeOH 194:3) gave the title compound (210 mg, 47%) as a red solid. 1H NMR (300 MHz, CDCl3) δ 4.60 (d, 2H, J=6.0 Hz), 7.07 (br s, 1H), 7.15 (d, 2H, J=8.4 Hz), 7.23 (d, 2H, J=8.7 Hz), 7.44-7.48 (m, 1H), 7.83 (ddd, 1H, J=7.5, 7.5, 1.8 Hz), 7.89 (d, 1H, J=7.8 Hz), 8.72 (d, 1H, J=4.5 Hz).

Sources & evidence

ORD record
ord-3a71f7687019404fa6b7c41991febe15
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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