Hydrochloric Acid → n-[(5-Chloro(2-thienyl))sulfonyl](4-nitrophenyl)carboxamide

HRID 900271Notes

Reaction equation

HRID 900271 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[OH-].[Na+].[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].Cl>CC(C)=O>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:20]([C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=2)=[O:21])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 14798Sodium HydroxideHCID 12413015-Chlorothiophene-2-Sulfonamide

Product 1

HCID 22064472n-[(5-Chloro(2-thienyl))sulfonyl](4-nitrophenyl)carboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 85 mg portion (0.43 mmol) of 5-chlorothiophenesulfonamide dissolved in 2 mL of acetone was treated with 110 μL of 4N NaOH (0.43 mmol) followed by addition of 80 mg (0.43 mmol) of 4-nitrobenzoyl chloride. After stirring for 12 h, the solution was acidfied 1N HCl and the precipitate was collected by filtration and dried. Recrystallization from EtOAc/hexane afforded 120 mg (81%) of the titled compound. ES-MS (M+H)+=347 (Cl).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customdried
  3. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-addee6c8b3454f4faf5a4a4485967fa5
Source dataset
uspto-grants-2008_04
Patent number
US07358257B2

Reaction notes

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