Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 178494278, compound

HRID 2261166Notes

Reaction equation

HRID 2261166 reaction equation
[CH3:1][O-:2].[Na+].S(O)(O)(=O)=O.[CH3:9][O:10][C:11]([NH2:13])=[NH:12].[C:14]([O:22]C)(=O)[CH2:15][C:16]([O:18]OC)=O>C(O)C>[CH3:9][O:10][C:11]1[N:13]=[C:14]([OH:22])[C:15]([O:2][CH3:1])=[C:16]([OH:18])[N:12]=1

Participants

5

Reactant 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 10942334Sodium MethoxideHCID 86618930HCID 86618930, compound

Product 1

HCID 178494278HCID 178494278, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

9.7 g (180 mmoles) of sodium methylate is added to a solution of 9 g (52 mmoles) of methoxyformamidine sulphate in 100 ml of ethanol cooled down to 0° C. and the mixture is stirred for 15 minutes; then a solution of 6.5 ml (46.8 mmoles) of methyl methoxy malonate in 50 ml of ethanol is added, followed by stirring overnight at ambient temperature. The reaction mixture is evaporated to dryness under reduced pressure (2 kPa). The residue is taken up in 100 ml of a saturated solution of sodium chloride and extracted with 800 and 200 ml of n-butanol. The organic phases are dried over sodium sulphate, filtered and evaporated to dryness under reduced pressure (2 kPa). 7 g of expected product is obtained in the form of a white solid.

Workup

  1. stirringby stirring overnight at ambient temperature
  2. customThe reaction mixture is evaporated to dryness under reduced pressure (2 kPa)
  3. extractionextracted with 800 and 200 ml of n-butanol
  4. dry with materialThe organic phases are dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure (2 kPa)

Sources & evidence

ORD record
ord-d4769d00700848f6b78512e7b9f8a8c0
Source dataset
uspto-grants-2010_12
Patent number
US07846932B2

Reaction notes

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