Acetamidine monohydrochloride → HCID 178439778, compound

HRID 1842578Notes

Reaction equation

HRID 1842578 reaction equation
[CH2:1]([CH:4]([C:9]([O:11]C)=O)[C:5]([O:7]C)=O)[C:2]#[CH:3].Cl.[C:14]([NH2:17])(=[NH:16])[CH3:15]>CO>[CH3:15][C:14]1[N:17]=[C:5]([OH:7])[C:4]([CH2:1][C:2]#[CH:3])=[C:9]([OH:11])[N:16]=1

Participants

4

Reactant 2

HCID 67170Acetamidine monohydrochlorideHCID 4620160Dimethyl propargylmalonate

Product 1

HCID 178439778HCID 178439778, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 250 mL flask was added 1 (3.96 g, 20 mmol), 2 (1.85 g, 20 mmol) and 50 mL anhydrous MeOH. After 800 mg (20 mmol) Na was added to the solution, yellow precipitate was observed. The resulting mixture was refluxed overnight. The yellow precipitate was collected by filtration and then dissolved in 10 mL H2O. The pH of the resulting solution was adjusted to 6.5 by adding 2 N HCl to afford a yellow precipitate, which was collected by filtration and dried over P2O5 to afford 1.21 g (37%) of 3: TLC Rf0.11 (CHCl3/MeOH 6:1); mp>300° C.; 1H NMR (DMSO-d6) δ 2.23 (s, 3 H), 3.05 (s, 2 H), 3.32 (s, 1 H), 11.92 (s, 2 H).

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. filtrationThe yellow precipitate was collected by filtration
  3. dissolutiondissolved in 10 mL H2O
  4. additionby adding 2 N HCl
  5. customto afford a yellow precipitate, which
  6. filtrationwas collected by filtration
  7. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-4f3a6081e57d44fd8ceaeda9e7adda5d
Source dataset
uspto-grants-2015_02
Patent number
US08946239B2

Reaction notes

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