Sodium Hydroxide → HCID 66971592, compound

HRID 1014061Notes

Reaction equation

HRID 1014061 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[NH:25][C:26]([NH:28][CH3:29])=[O:27].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>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[NH:25][C:26](=[O:27])[NH:28][CH3:29])[CH:10]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66877731HCID 66877731, compound

Product 1

HCID 66971592HCID 66971592, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Step 3) 2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (2.3 g), 1-[2-(aminomethyl)-4-chlorophenyl]-3-methylurea hydrochloride obtained in Step 2 (2.45 g) and diisopropylethylamine (5 ml) were stirred in ethanol (15 ml) overnight at 70° C. The reaction mixture was poured into 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated 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 ethanol, 4N hydrogen chloride-ethyl acetate solution (3 ml) was added, and the mixture was crystallized from ethanol-ethyl acetate. The precipitated crystals were collected by filtration, and recrystallized to give the title compound (0.52 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  7. dissolutionThe obtained residue was dissolved in ethanol
  8. addition4N hydrogen chloride-ethyl acetate solution (3 ml) was added
  9. customthe mixture was crystallized from ethanol-ethyl acetate
  10. filtrationThe precipitated crystals were collected by filtration
  11. customrecrystallized

Sources & evidence

ORD record
ord-85d5b30774e041638e9b1fb1561ae62b
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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