Cyanoacetamide → HCID 58056952, compound

HRID 455011Notes

Reaction equation

HRID 455011 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[C:15]([CH2:17][C:18]([NH2:20])=[O:19])#[N:16].[H-].[Na+].Cl.O1CCOCC1>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:17]([C:18](=[O:19])[NH2:20])[C:15]#[N:16])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

6

Reactant 4

HCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 58056952HCID 58056952, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Starting material 25 (10 g, 50 mmol) and cyanacetamide (26, 8.4 g, 100 mmol) were dissolved in dry THF and NaH (60% ig, 4 g, 100 mmol) was added. The reaction was stirred over night at ambient temperature. Now it was cooled to 0° C. and 4 N HCl/Dioxan was added. The reaction mixture was concentrated in vacuo, the solid residue crystallized with 400 ml isopropyl ethyl ether, resulting crystals were filtered and dried. Then the crystals were washed with water and again filtered and dried. Thereby 8.9 g of the desired product 27 (67%, 34 mmol) were isolated.

Workup

  1. temperatureNow it was cooled to 0° C.
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe solid residue crystallized with 400 ml isopropyl ethyl ether
  4. customresulting crystals
  5. filtrationwere filtered
  6. customdried
  7. washThen the crystals were washed with water
  8. filtrationagain filtered
  9. customdried

Sources & evidence

ORD record
ord-48946bbb0b774c688aca42a64732e121
Source dataset
uspto-grants-2013_07
Patent number
US08497283B2

Reaction notes

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