Potassium Carbonate → HCID 66969934, compound

HRID 447850Notes

Reaction equation

HRID 447850 reaction equation
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[NH2:16][CH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[S:25]([NH2:28])(=[O:27])=[O:26].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:16]([CH2:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[S:25](=[O:26])(=[O:27])[NH2:28])[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66877585HCID 66877585, compound

Product 1

HCID 66969934HCID 66969934, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.29 g), 2-(aminomethyl)-4-chlorobenzenesulfonamide hydrochloride (0.42 g) and potassium carbonate (0.52 g) were stirred in ethanol (10 ml) at 70° C. overnight. The reaction solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (30 mg).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  4. addition4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil
  5. filtrationthe precipitated crystals were collected by filtration
  6. customrecrystallized

Sources & evidence

ORD record
ord-64086a44fb664a27ba534d90e0a03270
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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