Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 178494173, compound

HRID 2085413Notes

Reaction equation

HRID 2085413 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:17])[C:15]=1[F:16])[CH:5]=[C:6]([C:10](=O)[CH3:11])[C:7](=[O:9])[CH3:8].S(O)(O)(=O)=O.[CH3:23][O:24][C:25](=[NH:27])[NH2:26].C([O-])(O)=O.[Na+]>CCO>[CH3:23][O:24][C:25]1[NH:27][CH:5]([C:4]2[CH:13]=[C:14]([F:17])[C:15]([F:16])=[C:2]([F:1])[CH:3]=2)[C:6]([C:7](=[O:9])[CH3:8])=[C:10]([CH3:11])[N:26]=1

Participants

5

Reactant 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 22725230HCID 22725230, compound

Product 1

HCID 178494173HCID 178494173, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
97.5 °C

Procedure

A mixture 3-(3,4,5-trifluorobenzylidene)-2,4-pentanedione (26.2 mmol), O-methylisourea hydrogen sulfate (3.22 g, 39.3 mmol), and NaHCO3 (6.6 g, 78.6 mmol) in EtOH (400 mL) was stirred and heated at 95-100° C. for 6 h. The mixture was filtered and the solid filter cake was washed with ethanol (100 mL). The solvent was evaporated from the combined filtrates and the crude product was purified by flash column chromatography (EtOAc/hexane, 1/9 to 1/4), to afford the desired product as an oil (2.80 g, 36%).

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe solid filter cake
  3. washwas washed with ethanol (100 mL)
  4. customThe solvent was evaporated from the combined filtrates
  5. customthe crude product was purified by flash column chromatography (EtOAc/hexane, 1/9 to 1/4)

Sources & evidence

ORD record
ord-b13afb9bd5b3485686d02af55d239b80
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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