Benzenesulfonyl chloride → HCID 19880978, compound

HRID 336097Notes

Reaction equation

HRID 336097 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:9]1([S:15]([O:8][N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=[O:1])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178526252HCID 178526252, compound

Product 1

HCID 19880978HCID 19880978, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Hydroxypyridine-1-oxide (1.0 g, 9.1 mmol) was reacted with benzenesulfonyl chloride (1.27 mL, 10.0 mmol) in 75 mL of pyridine to afford PZBG-1a in 77% yield (1.75 g, 7.0 mmol). 1H NMR (500 MHz, CDCl3) δ=8.02 (d, J=8.0 Hz, 2H), 7.75 (t, J=8.0 Hz, 1H), 7.59 (m, 3H), 7.28 (dt, J1=6.9 Hz, J2=2.3 Hz, 1H), 6.52 (d, J=9.8 Hz, 1H), 6.15 (t, J=7.5 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ=157.0, 139.7, 137.1, 136.0, 133.8, 130.0, 129.5, 123.4, 105.4. ESI-MS(+): m/z 252.01 [M+H]+, 273.95 [M+Na]+. Anal. calcd for C11H9NO4S: C, 52.58; H, 3.61; N, 5.57. Found: C, 52.21; H, 3.99; N, 5.44.

Workup

  1. customto afford PZBG-1a in 77% yield (1.75 g, 7.0 mmol)

Sources & evidence

ORD record
ord-4666f9ebf53e4f45bf137dba288b2bdb
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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