Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 178498444, compound

HRID 2085382Notes

Reaction equation

HRID 2085382 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:15](=O)[CH3:16])[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].S(O)(O)(=O)=O.[CH3:23][O:24][C:25](=[NH:27])[NH2:26].C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:27][C:25]([O:24][CH3:23])=[N:26][C:15]([CH3:16])=[C:10]2[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 54038767Methyl 2-{(3,4-difluorophenyl)methylene}-3-oxobutyrate

Product 1

HCID 178498444HCID 178498444, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 2-{(3,4-difluorophenyl)-methylene}-3-oxobutyrate (8.80 g, 36.3 mmol), O-methylisourea hydrogen sulfate (9.40 g, 546 mmol), and NaHCO3 (12.3 g, 146 mol) in DMF (30 mL) was heated at 70° C. with stirring for 16 h. The mixture was cooled, diluted with EtOAc (300 mL) and washed with water (5×300 mL), brine (300 mL), and dried over magnesium sulfate. The solvent was evaporated and the crude product was purified by flash chromatography (EtOAc/hexane, 1/9 to 3/7) as the gradient eluent, giving the desired product as an oil (3.82 g, 35%).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water (5×300 mL), brine (300 mL)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by flash chromatography (EtOAc/hexane, 1/9 to 3/7) as the gradient eluent

Sources & evidence

ORD record
ord-cab948308930424880014bf3def0d041
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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