Pyridine → HCID 178515557, compound

HRID 1779895Notes

Reaction equation

HRID 1779895 reaction equation
[C:1]([NH2:9])(=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:16](Cl)(=[O:25])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:2]1([C:1]2[NH:8][CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][C:16](=[O:25])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2332BenzamidineHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 178515557HCID 178515557, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 8.42 g (70.2 mmol) of benzamidine and 8 mL (99.2 mmol) of pyridine in 150 mL of toluene was added dropwise over 10 min a solution of 7.68 g (46.1 mmol) of cinnamoyl chloride in 20 mL of toluene. The mixture was stirred for 10 min at room temperature and heated at reflux for 2 days. The mixture was cooled, diluted with 150 mL of ethyl acetate and extracted with two 125 mL portions of 5% aqueous HCl. The combined aqueous HCl extracts were neutralized by careful addition of 50% aqueous NaOH and extracted with two 250 mL portions of ethyl acetate. These ethyl acetate extracts were combined, dried over MgSO4 and rotovaped to afford 7.80 g of 5,6-dihydro-2,6-diphenylpyrimidin-4-one as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 days
  3. temperatureThe mixture was cooled
  4. extractionextracted with two 125 mL portions of 5% aqueous HCl
  5. additionThe combined aqueous HCl extracts were neutralized by careful addition of 50% aqueous NaOH
  6. extractionextracted with two 250 mL portions of ethyl acetate
  7. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-242d39ad669b4935b314779b17ab2cad
Source dataset
uspto-grants-1997_05
Patent number
US05629264

Reaction notes

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