Ethyl Acetate → (2-[1,3]Dioxolan-2-yl4-methoxy-phenyl)-cyanamide

HRID 1456310Notes

Reaction equation

HRID 1456310 reaction equation
O1CCOC1[C:6]1[CH:7]=[C:8]([N:14]2[CH:18]=[N:17]N=N2)C=[CH:10][C:11]=1[O:12][CH3:13].C([Li])CCC.C(=O)(O)[O-].[Na+].[C:29]([O:32][CH2:33][CH3:34])(=[O:31])[CH3:30]>O1CCCC1.CCCCCC>[O:32]1[CH2:33][CH2:34][O:31][CH:29]1[C:30]1[CH:10]=[C:11]([O:12][CH3:13])[CH:6]=[CH:7][C:8]=1[NH:14][C:18]#[N:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 110430831-(3-[1,3]dioxolan-2-yl-4-methoxy-phenyl)-1H-tetrazoleHCID 178418339Butyllithium

Product 1

HCID 22106606(2-[1,3]Dioxolan-2-yl4-methoxy-phenyl)-cyanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1-(3-[1,3]dioxolan-2-yl-4-methoxy-phenyl)-1H-tetrazole (9.09 g) in dry tetrahydrofuran (200 ml) at -78° under nitrogen, n-butyl lithium solution in hexane (30 ml of 1.6 mol dm-3) was added. Nitrogen gas was evolved. After stirring under nitrogen for 5 min the mixture was allowed to warm to 0° over 10 min and 8% aqueous sodium bicarbonate (200 ml) was then added. After stirring for 10min ethyl acetate (150 ml) was added and the layers separated. The aqueous layer was then extracted with dichloromethane (2×200 ml) and the organic layers combined, dried (Na2SO4) and evaporated in vacuo to yield the title compound as an oil (8.0 g).

Workup

  1. temperatureto warm to 0° over 10 min
  2. additionwas added
  3. customthe layers separated
  4. extractionThe aqueous layer was then extracted with dichloromethane (2×200 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-803266f27a8f4835bbde8d53947898ee
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

Loading…