4-Nitrobenzenesulfonyl chloride → HCID 54767381, compound

HRID 336098Notes

Reaction equation

HRID 336098 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1)([O-:11])=[O:10]>N1C=CC=CC=1>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([S:18]([O:8][N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=[O:1])(=[O:20])=[O:19])=[CH:16][CH:17]=1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 178526252HCID 178526252, compound

Product 1

HCID 54767381HCID 54767381, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Hydroxypyridine-1-oxide (0.5 g, 4.5 mmol) was reacted with 4-nitrobenzenesulfonyl chloride (3.0 g, 13.5 mmol) in 40 mL of pyridine to afford PZBG-1c in 92% yield (1.23 g, 4.2 mmol). 1H NMR (500 MHz, CDCl3) δ=8.42 (d, J=8.6 Hz, 2H), 8.23 (d, J=9.2 Hz, 2H), 7.65 (dd, J1=7.5 Hz, J2=1.8 Hz, 1H), 7.34 (dt, J1=9.2 Hz, J2=1.7 Hz, 1H), 6.52 (d, J=9.2 Hz, 1H), 6.22 (t, J=7.7 Hz, 1H). 13C NMR (100 MHz, DMSO) δ=156.6, 152.3, 141.6, 139.4, 138.3, 131.8, 125.6, 122.8, 106.4. ESI-MS(+): m/z 297.28 [M+H]+, 319.02 [M+Na]+.

Workup

  1. customto afford PZBG-1c in 92% yield (1.23 g, 4.2 mmol)

Sources & evidence

ORD record
ord-3c5c41b58e2f496781be24d51ed26b11
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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