Benzamidine, hydrochloride → HCID 57839057, compound

HRID 732950Notes

Reaction equation

HRID 732950 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[CH:4]=[C:5]([C:10](=O)[CH3:11])[C:6]([O:8][CH3:9])=[O:7].Cl.[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC([O-])=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[CH:4]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:10]([CH3:11])[NH:27][C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:26]1

Participants

5

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 517045Sodium AcetateHCID 54009516Methyl 2-[(2,4-dichlorophenyl)methylidene]-3-oxobutanoate

Product 1

HCID 57839057HCID 57839057, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 2-(2,4-dichlorobenzylidene)-3-oxobutanoate (480 mg, 1.8 mmol) and benzamidine HCl salt (275 mg, 1.8 mmol) in DMF (6 mL) was added NaOAc (144 mg, 1.8 mmol). The reaction was heated to 60° C. for 3 days and was quenched by 1N HCl (10 mL). The reaction was diluted with EtOAc (10 mL) and the organic layer was washed with 1N HCl, saturated NH4Cl solution (10 mL) and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the crude product as a yellow oil (600 mg). The crude reaction product was moved onto next step without further purification.

Workup

  1. customwas quenched by 1N HCl (10 mL)
  2. additionThe reaction was diluted with EtOAc (10 mL)
  3. washthe organic layer was washed with 1N HCl, saturated NH4Cl solution (10 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c8afc35c77b4108b6915c84136cd3c3
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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