Triethylamine → Pyridine-2-sulfonic acid 4-chloromethyl-benzylamide

HRID 970931Notes

Reaction equation

HRID 970931 reaction equation
O[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CCN(CC)CC.CS([Cl:31])(=O)=O>>[Cl:31][CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68898056Pyridine-2-sulfonic acid 4-hydroxymethyl-benzylamide

Product 1

HCID 68899961Pyridine-2-sulfonic acid 4-chloromethyl-benzylamideYield 45.2%

Procedure

Reaction of pyridine-2-sulfonic acid 4-hydroxymethyl-benzylamide (140 mg, 0.50 mmol), Et3N (88 uL, 0.60 mmol), and MsCl (47 uL, 0.60 mmol) for 2 h at reflux followed by column chromatography on silica gel (CH2Cl2/MeOH 99:1) gave the title compound (67 mg, 45%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 4.28 (d, 2H, J=6.0 Hz), 4.54 (s, 2H), 5.17 (br s, 1H), 7.23-7.49 (m, 4H), 7.47-7.52 (m, 1H), 7.88 (ddd, 1H, J=7.5, 7.5, 1.7 Hz), 7.97 (d, 2H, J=7.5 Hz), 8.69 (d, 1H, J=4.8 Hz). ES-MS m/z 319 (M+Na).

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-e01c29ea235d4167ae20bfb595fe49af
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

Loading…