Acetone → (3-Formyl-4-methoxy-phenyl)-cyanamide

HRID 1456311Notes

Reaction equation

HRID 1456311 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([N:14]2[CH:18]=[N:17]N=N2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].Cl.CC(C)=O.C(=O)(O)[O-].[Na+]>O1CCCC1.CCCCCC.ClCCl>[CH:2]([C:6]1[CH:7]=[C:8]([NH:14][C:18]#[N:17])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])=[O:1]

Participants

8

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 110430831-(3-[1,3]dioxolan-2-yl-4-methoxy-phenyl)-1H-tetrazole

Product 1

HCID 22106573(3-Formyl-4-methoxy-phenyl)-cyanamideYield 95%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1-(3-[1,3]-dioxolan-2-yl4-methoxy-phenyl)-1H-tetrazole (0.46 g) in tetrahydrofuran (10 ml) at 0° under nitrogen n-butyl lithium (1.7 ml; a 1.6M solution in hexane) was added. After stirring for 5 min dilute aqueous hydrogen chloride solution (5 ml) and acetone (2ml) were added. The mixture was stirred for 1 h before addition of dichloromethane (30 ml) and 8% aqueous sodium bicarbonate solution (20 ml). The layers were separated and the aqueous layer extracted with dichloromethane (3×30 ml). The organic layers were combined, dried (Na2SO4), and evaporated to leave an orange solid. The material was washed with a small amount of ether and cyclohexane and dried in vacuo to yield the title compound as an orange solid (0.31 g).

Workup

  1. customat 0°
  2. additionwere added
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with dichloromethane (3×30 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto leave an orange solid
  8. washThe material was washed with a small amount of ether and cyclohexane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-ecdf28ae147c4b688943c03aa5871d3b
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

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