Benzamidine → HCID 136093747, compound

HRID 732957Notes

Reaction equation

HRID 732957 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:21]([NH2:29])(=[NH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CCO.C1CCCCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[C:4]1[N:28]=[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:29][C:11](=[O:13])[C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 2332BenzamidineHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12369938HCID 12369938, compound

Product 1

HCID 136093747HCID 136093747, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

A solution of diethyl 2-(2,4-dichlorobenzylidene)malonate (300 mg, 0.91 mmol) and benzamidine (134 mg, 0.91 mmol) in EtOH (3 mL) was heated to 60° C. for 2 hrs. The reaction was concentrated under reduced pressure. The resulting residue was dissolved in CH2Cl2 (4 mL) and DDQ (238 mg, 1.05 mmol) was added. After 1 hr, The reaction was diluted with cyclohexane/EtOAc solution (4:1, 100 mL) and the organic layer was extracted with saturated NaHCO3 solution (2×60 mL), brine (50 mL). The organic layer dried (MgSO4), filtered and concentrated under reduced pressure to give ethyl 4-(2,4-dichlorophenyl)-6-oxo-2-phenyl-1,6-dihydropyrimidine-5-carboxylate (372 mg, 100%) as a yellow solid. This product was moved onto next step without further purification.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in CH2Cl2 (4 mL)
  3. extractionthe organic layer was extracted with saturated NaHCO3 solution (2×60 mL), brine (50 mL)
  4. dry with materialThe organic layer dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8367580b45354c91a977b1b9ceae2665
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

Loading…