2-Chloroimidazoline sulfate → HCID 9883731, compound

HRID 890617Notes

Reaction equation

HRID 890617 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH:7][C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.S(O)(O)(=O)=O.Cl[C:26]1[NH:27][CH2:28][CH2:29][N:30]=1>CC(O)C>[NH:30]1[CH2:29][CH2:28][N:27]=[C:26]1[NH:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH:7][C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 125033982-Chloroimidazoline sulfateHCID 22246045HCID 22246045, compound

Product 1

HCID 9883731HCID 9883731, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-(4-Aminobenzyl)-4-methoxybenzamide (15 g, 58.4 mmol), 2-chloroimidazoline sulfate (15.2 g, 74 mmol) and 2-propanol (380 mL) was heated at reflux for 2.5 h under N2. The mixture was cooled to 0° C. and filtered, and the filtrate was concentrated to dryness. To the resulting residue 10% aqueous sodium hydroxide was added to reach pH 13-14. The resulting suspension was filtered, and the solid N-[4-(4,5-dihydro-1H-imidazol-2-ylamino)-benzyl]-4-methoxybenzamide was crystallized from dichloromethane. Weight 11.9 g (61.4% yield). mp 160.3-160.6° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h under N2
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to dryness
  5. additionTo the resulting residue 10% aqueous sodium hydroxide was added
  6. filtrationThe resulting suspension was filtered
  7. customthe solid N-[4-(4,5-dihydro-1H-imidazol-2-ylamino)-benzyl]-4-methoxybenzamide was crystallized from dichloromethane

Sources & evidence

ORD record
ord-a4fa844e4f3240a9af46f2274a672dee
Source dataset
uspto-grants-2006_02
Patent number
US06998414B2

Reaction notes

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