Water → (E)-2-pyridin-3-yl-ethenesulfonic acid 2,4-dichloro-benzoylamide

HRID 1272078Notes

Reaction equation

HRID 1272078 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5](/[CH:9]=[CH:10]/[S:11]([NH2:14])(=[O:13])=[O:12])[CH:4]=1.[Cl:15][C:16]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].O>O1CCOCC1>[Cl:15][C:16]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:17]=1[C:18]([NH:14][S:11](/[CH:10]=[CH:9]/[C:5]1[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=1)(=[O:12])=[O:13])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 666452,4-Dichlorobenzoyl chlorideHCID 14912437(E)-2-pyridin-3-yl-ethenesulfonic acid amide

Product 1

HCID 16036106(E)-2-pyridin-3-yl-ethenesulfonic acid 2,4-dichloro-benzoylamideYield 27.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil) (36 mg, 0.9 mmol) was added to a solution of (E)-2-Pyridin-3-yl-ethenesulfonic acid amide (56 mg, 0.3 mmol) in dioxane (1 mL) and the mixture was shaken for 30 minutes. A solution of 2,4-dichlorobenzoyl chloride (63 μL, 0.45 mmol) in dioxane (0.5 mL) was added to the mixture and the whole was shaken at room temperature for 18 hours. Water (0.1 mL) was added to the mixture and the whole was concentrated in vacuo. The resultant residue was purified by preparative HPLC to give (E)-2-pyridin-3-yl-ethenesulfonic acid 2,4-dichloro-benzoylamide (29.1 mg, 26%) as sodium salt.

Workup

  1. stirringthe whole was shaken at room temperature for 18 hours
  2. concentrationthe whole was concentrated in vacuo
  3. customThe resultant residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-141d8adc68d04442b43d3acfffaaa126
Source dataset
uspto-grants-2007_04
Patent number
US07208506B2

Reaction notes

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