Hydrochloric Acid → HCID 178518205, compound

HRID 1912645Notes

Reaction equation

HRID 1912645 reaction equation
[CH2:1]([O:8][CH:9]([C:14]([O:16]C)=O)[C:10](OC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl.[CH:22]([NH2:24])=[NH:23].Cl>CO>[CH2:1]([O:8][C:9]1[C:14]([OH:16])=[N:23][CH:22]=[N:24][C:10]=1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 14919765Dimethyl (benzyloxy)propanedioate

Product 1

HCID 178518205HCID 178518205, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Dimethyl 2-(benzyloxy)malonate (16.1 g, 0.0675 mol) was dissolved in MeOH (27 ml), NaOMe (42.59 ml of a 30% solution in MeOH, 3.5 eq) was added and the mixture cooled to 0 C. Formamidine hydrochloride (5.68 g, 1.05 eq) was added and the mixture stirred at 0° C. for 30 minutes and then at reflux for 2 hours. After cooling to 0° C. concentrated HCl (21 ml) was added and the solid was collected by filtration (washing with cold water 3×20 ml) to give 15.14 g of the title compound.

Workup

  1. temperaturethe mixture cooled to 0 C
  2. temperatureat reflux for 2 hours
  3. additionwas added
  4. filtrationthe solid was collected by filtration (washing with cold water 3×20 ml)

Sources & evidence

ORD record
ord-88bf14dae5544a44981b29a16f64d508
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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