Water → (E)-2-(2-chloro-phenyl)-ethenesulfonic acid 4-bromo-2-chloro-benzoylamide

HRID 1272363Notes

Reaction equation

HRID 1272363 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1/[CH:10]=[CH:11]/[S:12]([NH2:15])(=[O:14])=[O:13].[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[C:19]([Cl:26])[CH:18]=1.O>O1CCOCC1>[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:15][S:12](/[CH:11]=[CH:10]/[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[Cl:3])(=[O:13])=[O:14])=[O:22])=[C:19]([Cl:26])[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 110203382-(2-Chlorophenyl)ethene-1-sulfonamideHCID 155922074-Bromo-2-chlorobenzoyl chloride

Product 1

HCID 15603095(E)-2-(2-chloro-phenyl)-ethenesulfonic acid 4-bromo-2-chloro-benzoylamide

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-(2-chloro-phenyl)-ethenesulfonic acid amide (65 mg, 0.3 mmol) in 1,4-dioxane (1.5 mL) and the reaction mixture was shaken for 30 minutes. Crude 4-bromo-2-chloro-benzoyl chloride (114 mg, 0.45 mmol) in dioxane (0.5 mL) was added and the reaction mixture was shaken at room temperature for 18 hours. Water (0.1 mL) was added to the reaction mixture and the whole was concentrated in vacuo. The resultant residue was purified by preparative HPLC under neutral conditions to give (E)-2-(2-chloro-phenyl)-ethenesulfonic acid 4-bromo-2-chloro-benzoylamide; sodium salt (38 mg, 29% yield).

Workup

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

Sources & evidence

ORD record
ord-c48f4735e72e4660a31253ed29dcc3c7
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

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