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

HRID 1612314Notes

Reaction equation

HRID 1612314 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-6cb9279fd3784fa2859bc5211328dba4
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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