Dichloromethane → HCID 54767383, compound

HRID 336100Notes

Reaction equation

HRID 336100 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].Cl[S:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11].ClCCl.C(OCC)(=O)C>N1C=CC=CC=1>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[O:8][S:10]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:20][CH:21]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 823854-(Chlorosulfonyl)benzoic acidHCID 178526252HCID 178526252, compound

Product 1

HCID 54767383HCID 54767383, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Hydroxypyridine-1-oxide (0.21 g, 1.9 mmol) was reacted with 4-(chlorosulfonyl)benzoic acid (0.62 g, 2.8 mmol) in 5 mL pyridine. The solvent was evaporated, leaving a yellow oil. Addition of 5 mL of dichloromethane followed by the addition of 5 mL of ethyl acetate allowed for precipitation of PZBG-1e in 30% yield (0.17 g, 0.57 mmol). 1H NMR (400 MHz, DMSO) δ=8.18 (d, J=8.8 Hz, 2H), 8.08 (d, J=8.4 Hz), 7.88 (dd, J1=7.6 Hz, J2=2 Hz), 7.45 (td, J1=8.2 Hz, J2=2 Hz, 1H), 6.50 (dd, J1=9.2 Hz, J2=1.6 Hz, 1H), 6.26 (td, J1=7 Hz, J2=1.6 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ=166.5, 156.6, 141.5, 138.2, 137.9, 137.3, 131.2, 130.4, 122.8, 106.2. ESI-MS(−): m/z 294.26[M−H]−. Anal. calcd. for C12H9NO6S: C, 48.81; H, 3.07; N, 4.74. Found: C, 48.91; H, 3.37; N, 4.84.

Workup

  1. customThe solvent was evaporated
  2. customleaving a yellow oil
  3. customallowed for precipitation of PZBG-1e in 30% yield (0.17 g, 0.57 mmol)

Sources & evidence

ORD record
ord-dbd7bb6a3d7740f79e905842f6361d5d
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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