2-Methyl-2-thiopseudourea → HCID 178418413, compound

HRID 1783504Notes

Reaction equation

HRID 1783504 reaction equation
C([O:3][CH:4]=[C:5]([C:11]#[N:12])[C:6](OCC)=O)C.[CH3:13][S:14][C:15](=[NH:17])[NH2:16].C[O-].[Na+].[Na]>CO>[OH:3][C:4]1[C:5]([C:11]#[N:12])=[CH:6][N:16]=[C:15]([S:14][CH3:13])[N:17]=1

Participants

6

Reactant 4

HCID 51422-Methyl-2-thiopseudoureaHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 178418413HCID 178418413, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 5° C. solution of 119 g (703 mmol) of freshly distilled ethyl (ethoxymethylene)cyanoacetate in 800 mL of methanol is added 108 g (599 mmol) of 2-methyl-2-thiopseudourea. To this mixture is added a solution of sodium methoxide prepared by dissolving 35.6 g (1.55 mol) of sodium metal in 800 mL of methanol. The solution is warmed to room temperature and stirred for 6 hours. After standing overnight, the solvent is removed under reduced pressure, the residue is dissolved in 1.5 L of water at 50° C. with stirring, and the solution is filtered hot. The filtrate is acidified to pH 2 with concentrated HCl and kept at room temperature overnight. The precipitated product is collected and dried to give 48.3 g (48%) of the title compound, which is used directly in the next step.

Workup

  1. customprepared
  2. waitAfter standing overnight
  3. customthe solvent is removed under reduced pressure
  4. dissolutionthe residue is dissolved in 1.5 L of water at 50° C.
  5. stirringwith stirring
  6. filtrationthe solution is filtered hot
  7. waitkept at room temperature overnight
  8. customThe precipitated product is collected
  9. customdried

Sources & evidence

ORD record
ord-b1ab0efff526456f88e8e045e28b22b0
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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