Water → 7-Oxocyclohepta-1,3,5-trien-1-yl 4-nitrobenzenesulfonate

HRID 336111

Reaction equation

HRID 336111 reaction equation
[OH:1][C:2]1[C:3](=[O:9])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1.[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].O>N1C=CC=CC=1>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([O:9][C:3]2[C:2](=[O:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 10789Tropolone

Product 1

HCID 866603597-Oxocyclohepta-1,3,5-trien-1-yl 4-nitrobenzenesulfonateYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Hydroxycyclohepta-2,4,6-trienone (0.2 g, 1.7 mmol) was reacted with 4-nitrobenzenesulfonyl chloride (1.1 g, 4.9 mmol) in 5 mL of pyridine. Addition of 10 mL of water allowed for precipitation of PZBG-4c in 71% yield (0.38 g, 1.2 mmol) without the need for further purification. 1H NMR (400 MHz, DMSO) δ=8.45 (d, J=8.8 Hz, 2H), 8.22 (d, J=8.8 Hz, 2H), 7.52 (d, J=9.2 Hz, 1H), 7.46 (dd, J1=10.2 Hz, J2=3.6 Hz, 1H), 7.31 (dd, J1=9.8 Hz, J2=2 Hz, 1H), 7.15 (dd, J1=10.6 Hz, J2=3.6 Hz, 1H). 13C (100 MHz, CDCl3) δ=179.09, 154.86, 151.50, 141.95, 141.27, 138.59, 136.87, 132.06, 131.48, 130.42, 125.42. ESI-MS(+): m/z 308.01 [M+H]+, 324.73 [M+NH4]+

Workup

  1. customallowed for precipitation of PZBG-4c in 71% yield (0.38 g, 1.2 mmol) without the need
  2. customfor further purification

Sources & evidence

ORD record
ord-9c6062c339ca40849b9f819f26ca3350
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Linked notes

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