4-Chlorobenzylamine → HCID 178470383, compound

HRID 1419697Notes

Reaction equation

HRID 1419697 reaction equation
[N:1](=[C:3]([C:9]([CH3:11])=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])O.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>CC#N>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]2[NH:1][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:9]([CH3:11])[N:18]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178472877HCID 178472877, compound

Product 1

HCID 178470383HCID 178470383, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 2-oximinoacetoacetate (6 g, 38 mmol; obtained according to Org.Synth. 1941, 21, 67) in MeCN (75 mL) was treated with 4-chlorobenzylamine (5.6 g, 40 mmol) at reflux for 18 h. Next, the reaction mixture was allowed to cool and the yellow solid formed was collected by filtration to give ethyl 2-(4-chlorophenyl)-5-methyl-3H-imidazole-4-carboxylate as a white solid (4.1 g, 40%): mp 237°-238° C.; 1H NMR (300 MHz, DMSO--d6) δ (DMSO) 7.96 (d, J=8, 2H, arom), 7.57 (d, J=8, 2H, arom), 4.27 (q, J=7, 2H, OCH2), 2.54 (s, 3H, Me-imidazole), 1.33 (t, J=7, 3H, OCH2CH3). Analysis calculated for C13H13ClN2O2 : C 58.99; H 4.95; N 10.58. Found: C 59.20; H 4.95; N 10.59.

Workup

  1. temperatureat reflux for 18 h
  2. temperatureto cool
  3. customthe yellow solid formed
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-87777bb7b49349d89d526079c2ac6d41
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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