Formamidine acetate → HCID 178420880, compound

HRID 365493Notes

Reaction equation

HRID 365493 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][CH:12]([NH2:15])[CH2:13][NH2:14].[C:16](O)(=O)C.C(N)=N.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>CCO>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][CH:12]1[CH2:13][NH:14][CH:16]=[N:15]1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 444972Fumaric AcidHCID 10703303HCID 10703303, compound

Product 1

HCID 178420880HCID 178420880, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture composed of 0.505 g (2.5 mmol) of the compound obtained in Step 4 and 0.286 g (2.75 mmol) of formamidine acetate in 20 ml of EtOH is stirred at 20° C. for 16 hours. After evaporating off the solvent, the residue is taken up in 10 ml of CH2Cl2 ; the mixture is treated with 5 ml of 2N NaOH and extracted with CH2Cl2 (3×20 ml). The combined organic phases are dried and concentrated; the residual oil is dissolved in 10 ml of EtOH and the mixture is treated with a solution of 0.29 g (2.5 mmol) of fumaric acid in 5 ml of EtOH. The title compound is isolated after recrystallisation.

Workup

  1. customAfter evaporating off the solvent
  2. additionthe mixture is treated with 5 ml of 2N NaOH
  3. extractionextracted with CH2Cl2 (3×20 ml)
  4. customThe combined organic phases are dried
  5. concentrationconcentrated
  6. dissolutionthe residual oil is dissolved in 10 ml of EtOH

Sources & evidence

ORD record
ord-629868ff945d4b50b900976ece65b7e7
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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