1,4-Dioxane → HCID 57460763, compound

HRID 1674152Notes

Reaction equation

HRID 1674152 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].[O-]CC.[Na+].[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([C:31](OCC)=[O:32])[C:26](OCC)=[O:27])=[CH:20][CH:19]=1)#[N:11].O1CCOCC1>C(O)C>[OH:32][C:31]1[N:4]=[C:2]([CH3:3])[NH:5][C:26](=[O:27])[C:25]=1[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[C:12]([C:10]#[N:11])=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 57460762HCID 57460762, compound

Product 1

HCID 57460763HCID 57460763, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of acetamidine hydrochloride (2.68 g) in ethanol (30 mL) were added sodium ethoxide (20% ethanol solution, 14.5 g) and then a solution of diethyl [(2′-cyanobiphenyl-4-yl)methyl]malonate in ethanol (30 mL)-1,4-dioxane (15 mL) at 0° C., and the reaction mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated, and the residue was adjusted to pH 5 with water (50 mL) and 50% aqueous acetic acid solution. The obtained crystallized product was collected by filtration and washed with water to give the title compound as colorless crystals (1.8 g, 40%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe obtained crystallized product
  3. filtrationwas collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-fae977bfbbf542f19c3c8f7b02a03bed
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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