1-Iodopropane → (E)-1-phenyl-N-(1-propylimidazol-2-yl)methanimine

HRID 1824229Notes

Reaction equation

HRID 1824229 reaction equation
[C:1]1(/[CH:7]=[N:8]/[C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]([O-])(C)[CH3:16].[K+].ICCC>CN(C=O)C.O>[C:1]1(/[CH:7]=[N:8]/[C:9]2[N:13]([CH2:14][CH2:15][CH3:16])[CH:12]=[CH:11][N:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 336431-IodopropaneHCID 22147335(E)-N-(1H-imidazol-2-yl)-1-phenylmethanimineHCID 23665647Potassium tert-butoxide

Product 1

HCID 22147424(E)-1-phenyl-N-(1-propylimidazol-2-yl)methanimineYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[(1E)-phenylmethylidene]-1H-imidazol-2-amine (1.00 g, 5.84 mmol) in DMF (20 mL) was added KOt-Bu (0.80 g, 7.13 mmol) and 1-iodopropane (0.63 mL, 6.46 mmol). After 3.5 h, the reaction was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with heptanes/EtOAc (2:1) to give 1.12 g (90%) of yellow liquid: 1H NMR (400 MHz, CDCl3) δ 9.23, 7.94, 7.47, 7.02, 6.94, 4.14, 1.83, 0.95; IR (liq.) 2966, 2935, 2876, 1612, 1576, 1509, 1477, 1450, 1313, 1282, 1150, 761, 738, 716, 690 cm−1; HRMS (FAB) calcd for C13H15N3+H 214.1344, found 214.1336.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (Biotage, 40M) with heptanes/EtOAc (2:1)

Sources & evidence

ORD record
ord-894fc792e8c34379bd7eaeef8251d9ba
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

Loading…