Cyanamide → HCID 86093112, compound

HRID 1294703Notes

Reaction equation

HRID 1294703 reaction equation
F[B-](F)(F)F.C(O[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])=[NH2+:10])C.[O-]CC.[Na+].[N:22]#[C:23][NH2:24]>C(O)C>[C:23]([N:24]=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[NH2:10])#[N:22]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 2723922Sodium ethoxideHCID 87822113HCID 87822113, compound

Product 1

HCID 86093112HCID 86093112, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of Example 19A (2.5 g 10.00 mmol) in 10 ml of absolute ethanol was added a solution of sodium ethoxide (681 mg, 10 mmol) in 3.7 ml of absolute ethanol. The precipitate was filtered and the filtrate was treated with a solution of cyanamide (420 mg, 10 mmol) in 10 ml of absolute ethanol. The reaction mixture was refluxed for 3 days and the solvent removed under reduced pressure. The crude mixture was purified by silica gel chromatography, eluting with a gradient of 0-50% ethyl acetate in methylene chloride to provide the 0.3 g of title compound. MS (ESI+) m/z 160 (M+H)+.

Workup

  1. filtrationThe precipitate was filtered
  2. temperatureThe reaction mixture was refluxed for 3 days
  3. customthe solvent removed under reduced pressure
  4. customThe crude mixture was purified by silica gel chromatography
  5. washeluting with a gradient of 0-50% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-1931ed61321c422e968827a2b5da7d87
Source dataset
uspto-grants-2007_07
Patent number
US07241776B2

Reaction notes

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