Hydrochloric Acid → (E)-2-thiophen-2-yl-ethenesulfonic acid 2,4-dichloro-benzoylamide

HRID 1272074Notes

Reaction equation

HRID 1272074 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(=O)([O-])[O-].[K+].[K+].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1/[CH:23]=[CH:24]/[S:25]([NH2:28])(=[O:27])=[O:26].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:28][S:25](/[CH:24]=[CH:23]/[C:19]1[S:18][CH:22]=[CH:21][CH:20]=1)(=[O:27])=[O:26])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 666452,4-Dichlorobenzoyl chlorideHCID 149124362-(Thiophen-2-yl)ethene-1-sulfonamide

Product 1

HCID 11990600(E)-2-thiophen-2-yl-ethenesulfonic acid 2,4-dichloro-benzoylamideYield 29%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Dichlorobenzoyl chloride (53 μL, 0.375 mmol) was added to a mixture of potassium carbonate (69 mg, 0.5 mmol) and (E)-2-thiophen-2-yl-ethenesulfonic acid amide (47 mg, 0.25 mmol) in 1,4-dioxane (1.5 mL) at ambient temperature. The mixture was heated at 80° C. for 16 hours then allowed to cool to room temperature whereupon 1N HCl (2 mL) was added in one portion. The mixture was extracted with ethyl acetate (2 mL) and the organics were dried with MgSO4, filtered and concentrated in vacuo. The resultant residue was purified by preparative HPLC to afford (E)-2-thiophen-2-yl-ethenesulfonic acid 2,4-dichloro-benzoylamide (26.3 mg, 29%).

Workup

  1. additionwas added in one portion
  2. extractionThe mixture was extracted with ethyl acetate (2 mL)
  3. dry with materialthe organics were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-18323cd34c984bd0b4c02c03498bb157
Source dataset
uspto-grants-2007_04
Patent number
US07208506B2

Reaction notes

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