Benzenesulfonyl chloride, 2,4-dinitro- → 2-Oxopyridin-1(2H)-yl 2,4-dinitrobenzenesulfonate

HRID 336099

Reaction equation

HRID 336099 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]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[S:21](Cl)(=[O:23])=[O:22])([O-:11])=[O:10]>N1C=CC=CC=1>[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[S:21]([O:8][N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]1=[O:1])(=[O:23])=[O:22])([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 74255Benzenesulfonyl chloride, 2,4-dinitro-HCID 178526252HCID 178526252, compound

Product 1

HCID 547673822-Oxopyridin-1(2H)-yl 2,4-dinitrobenzenesulfonateYield 31%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Hydroxypyridine-1-oxide (0.5 g, 4.5 mmol) was reacted with 2,4-dinitrobenzenesulfonyl chloride (1.32 g, 5.0 mmol) in 40 mL of pyridine to afford PZBG-1d in 31% yield (0.48 g, 1.4 mmol). 1H NMR (500 MHz, CDCl3) δ=8.96 (d, J=2.3 Hz, 1H), 8.42 (dd, J1=9.2 Hz, J2=2.3 Hz, 1H), 7.68 (dd, J1=6.9 Hz, J2=1.7 Hz, 1H), 7.50 (dt, J1=7.5 Hz, J2=2.3 Hz, 1H), 7.06 (d, J=8.1 Hz, 1H), 6.82 (dd, J1=9.2 Hz, J2=1.8 Hz, 1H), 6.35 (dt, J1=6.9 Hz, J2=1.8 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ=157.0, 155.6, 140.5, 135.1, 129.6, 124.0, 122.9, 116.0, 106.6.

Workup

  1. customto afford PZBG-1d in 31% yield (0.48 g, 1.4 mmol)

Sources & evidence

ORD record
ord-ae68e42c4c2a471caff5420acccf6bcf
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Linked notes

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