4-Nitrobenzenesulfonyl chloride → HCID 86660352, compound

HRID 336103Notes

Reaction equation

HRID 336103 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9].[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11]>N1C=CC=CC=1>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([O:1][C:2]2[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=2[CH3:9])(=[O:21])=[O:20])=[CH:17][CH:18]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8369Maltol

Product 1

HCID 86660352HCID 86660352, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Hydroxy-2-methyl-4H-pyran-4-one (0.5 g, 4.0 mmol) was reacted with 4-nitrobenzenesulfonyl chloride (0.88 g, 4.0 mmol) in 15 mL of pyridine to afford PZBG-2c in 58% yield (0.71 g, 2.3 mmol). 1H NMR (500 MHz, CDCl3) δ=8.42 (d, J=9.2 Hz, 2H), 8.31 (d, J=9.2 Hz, 2H), 7.69 (d, J=5.7 Hz, 1H), 6.34 (d, J=5.8 Hz, 1H), 2.53 (s, 3H, CH3). 13C NMR (100 MHz, CDCl3) δ=171.8, 163.5, 154.6, 151.2, 142.3, 138.6, 130.4, 124.3, 117.6, 16.3. ESI-MS(+): m/z 312.06 [M+H]+.

Workup

  1. customto afford PZBG-2c in 58% yield (0.71 g, 2.3 mmol)

Sources & evidence

ORD record
ord-5edf8c11ec084a0fa72d05946e1b76e2
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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