Potassium Carbonate → HCID 66969805, compound

HRID 1015869Notes

Reaction equation

HRID 1015869 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]([F: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]([F: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 66878437HCID 66878437, compound

Product 1

HCID 66969805HCID 66969805, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Step 4) 2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (1.0 g), 2-(aminomethyl)-4-fluorobenzenesulfonamide hydrochloride obtained in Step 3 (1.23 g) and potassium carbonate (1.76 g) were stirred in ethanol (20 ml) overnight at 70° C. 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 (68 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-ee69b71f52cc446cbed9ffffeb35def8
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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