Hydrochloric Acid → HCID 178500110, compound

HRID 2088870Notes

Reaction equation

HRID 2088870 reaction equation
[CH3:1][O-].[Na+].CO[C:6](=O)[CH2:7][C:8]([O:10][CH3:11])=[O:9].C([O:18][CH3:19])(=O)/C=C/C.[C:20]([OH:23])(=O)[CH3:21].[CH:24]([NH2:26])=[NH:25].Cl>CO>[OH:23][C:20]1[C:21]([CH:6]([CH3:1])[CH2:7][C:8]([O:10][CH3:11])=[O:9])=[C:19]([OH:18])[N:26]=[CH:24][N:25]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 160693Formamidine acetateHCID 638132Methyl CrotonateHCID 10942334Sodium Methoxide2×

Product 1

HCID 178500110HCID 178500110, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Add sodium methoxide (14.69 g, 0.85 eq) to methanol (70 mL). Heat to reflux over 15 minutes while adding a mixture of propanedioic acid dimethyl ester (36.64 mL, 320.00 mmol) and methyl crotonate (34.01 mL, 1.0 eq). Reflux the mixture for 40 minutes, then allow the mixture to cool to room temperature. Add a mixture of sodium methoxide (19.02 g, 1.1 eq), methanol (70 mL) and formamidine acetate (39.98 g, 1.2 eq). Stir at room temperature overnight. Cool the mixture in an ice bath and add 5 M aqueous hydrochloric acid, adjusting the pH to 3. Filter to give the title compound (41.00 g, 60%). MS (ES) m/z=213 [M]+.

Workup

  1. temperatureHeat
  2. temperatureto reflux over 15 minutes
  3. additionwhile adding
  4. temperatureReflux the mixture for 40 minutes
  5. additionAdd
  6. temperatureCool the mixture in an ice bath
  7. filtrationFilter

Sources & evidence

ORD record
ord-d6472cda85bb432887132cd78c1fbb2b
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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