Benzaldehyde → (E)-N-(1H-imidazol-2-yl)-1-phenylmethanimine

HRID 2266782Notes

Reaction equation

HRID 2266782 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(O)(O)(=O)=O.[NH2:14][C:15]1[NH:16][CH:17]=[CH:18][N:19]=1.C(N(CC)CC)C>ClCCl.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[NH:16]1[CH:17]=[CH:18][N:19]=[C:15]1/[N:14]=[CH:1]/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 135136Bis(2-amino-1H-imidazole) sulphate

Product 1

HCID 22147335(E)-N-(1H-imidazol-2-yl)-1-phenylmethanimine

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzaldehyde (1.92 ml, 18.8 mmol) in dichloromethane (15 ml) were added sequentially 2-aminoimidazole sulfate (3.77 g, 14.3 mmol), tetraisopropyl orthotitanate (6.83 ml, 23.3 mmol) and triethylamine (3.90 ml, 2.81 mmol). The reaction mixture was stirred at room temperature for 16 hours and then concentrated in vacuo. The residue was taken up in ethyl acetate and water and the mixture filtered. The filtrate phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo to yield the title compound as a yellow solid which was used in the next step without further purification (3.03 g, 95%); MS (ISP): 172.1 ([M+H]+).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationwater and the mixture filtered
  3. customThe filtrate phases were separated
  4. dry with materialthe organic phase dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d73b39ca631c421aaf6f9a06e81219cd
Source dataset
uspto-grants-2010_12
Patent number
US07858653B2

Reaction notes

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