Potassium Carbonate → HCID 66969827, compound

HRID 1014031Notes

Reaction equation

HRID 1014031 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].[NH2:15][CH2:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[S:24]([NH:27][CH2:28][CH3:29])(=[O:26])=[O:25].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:15]([CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[S:24](=[O:26])(=[O:25])[NH:27][CH2:28][CH3:29])[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66876867HCID 66876867, compound

Product 1

HCID 66969827HCID 66969827, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(Step 2) A suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.19 g), 2-(aminomethyl)-N-ethyl-4-fluorobenzenesulfonamide obtained in Step 1 (0.23 g) and potassium carbonate (0.34 g) in ethanol (10 ml) was stirred overnight at 70° C. The reaction solution was filtered through celite, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). The obtained residue was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (1 ml) was added, and the mixture was crystallized from methanol-ethyl acetate. The precipitated crystals were collected by filtration, and recrystallized from methanol-ethyl acetate to give the title compound (0.04 g).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  4. dissolutionThe obtained residue was dissolved in methanol
  5. addition4N hydrogen chloride-ethyl acetate solution (1 ml) was added
  6. customthe mixture was crystallized from methanol-ethyl acetate
  7. filtrationThe precipitated crystals were collected by filtration
  8. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-72a5cc7f289949d7b4cd73ba422a69cd
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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