Triethylamine → HCID 85814299, compound

HRID 970928Notes

Reaction equation

HRID 970928 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])=[CH:5][CH:4]=1.CCN(CC)CC.CS([Cl:29])(=O)=O>>[Cl:29][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 64792821HCID 64792821, compound

Product 1

HCID 85814299HCID 85814299, compoundYield 95.1%

Procedure

Reaction of Pyridine-2-carboxylic acid (4-hydroxymethyl-phenyl)amide (342 mg, 1.50 mmol), Et3N (262 uL, 1.80 mmol), and methanesulfonylchloride (128 uL, 1.65 mmol) for 2 h at reflux gave the title compound (352 mg, 95%) as a red solid. 1H NMR (300 MHz, CDCl3) δ 4.61 (s, 2H), 7.45 (d, 2H, J=8.4 Hz), 7.50 (ddd, 1H, J=7.5, 4.8, 0.9 Hz), 7.80 (d, 2H, J=8.7 Hz), 7.92 (ddd, 1H, J=7.8, 7.8, 1.6 Hz), 8.63 (d, 1H, J=6.0 Hz), 10.08 (br s, 1H).

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-933fdf81651a4dbd9b19f6aad3a9ddc8
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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