HCID 69419623, compound → HCID 21113074, compound

HRID 1766983Notes

Reaction equation

HRID 1766983 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[N:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:10]=1[CH:11]=[N:12][NH2:13])=[O:5])C>C(O)(=O)C.C1(C)C=CC=CC=1>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:8]1[N:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:10]2[CH:11]=[N:12][NH:13][C:4](=[O:5])[C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 69419623HCID 69419623, compound

Product 1

HCID 21113074HCID 21113074, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-hydrazonomethyl-1H-imidazole-4-carboxylic acid ethyl ester (I-2f, 54 mg, 0.134 mmol) and glacial acetic acid (1 drop) in toluene (3 ml) was heated under reflux for 18 hours, at which time a white solid precipitated out of solution. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was purified via 1 mm chromatotron plates using 100% EtOAc as solvent to give the desired product (I-2g) as a white solid (22 mg): +APCI MS (M+1) 357.1; 1H NMR (CD2Cl2) δ 7.18–7.48 (8H, m), 8.01 (1H, s), 10.60 (1H, s).

Workup

  1. temperatureunder reflux for 18 hours, at which time a white solid
  2. customprecipitated out of solution
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified via 1 mm chromatotron plates

Sources & evidence

ORD record
ord-60b5144ac4ec4b76acb48aa4812e0495
Source dataset
uspto-grants-2007_06
Patent number
US07232823B2

Reaction notes

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