Potassium Carbonate → 2-[4-(4-Dimethylaminosulfonylbenzyl)-phenyl]amino-imidazoline

HRID 1358823Notes

Reaction equation

HRID 1358823 reaction equation
[CH3:1][N:2]([CH3:20])[S:3]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].S(O)(O)(=O)=O.Cl[C:27]1[NH:28][CH2:29][CH2:30][N:31]=1.C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[CH3:20][N:2]([CH3:1])[S:3]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:27]3[NH:31][CH2:30][CH2:29][N:28]=3)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 125033982-Chloroimidazoline sulfateHCID 218770384-(4-Dimethylaminosulfonylbenzyl)-phenylamine

Product 1

HCID 120943872-[4-(4-Dimethylaminosulfonylbenzyl)-phenyl]amino-imidazolineYield 164.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(4-dimethylaminosulfonylbenzyl)-phenylamine (288 mg) and 2-chloro-imidazoline sulfate (110 mg) in 2-propanol was heated under reflux for 16 hours. A dilute solution of potassium carbonate was poured into the mixture and extracted with dichloromethane (4×15 mL). Solvents were evaported to give 2-[4-(4-dimethylaminosulfonylbenzyl)-phenyl]amino-imidazoline as a solid (320 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. extractionextracted with dichloromethane (4×15 mL)

Sources & evidence

ORD record
ord-dead42ba181b413a97774bc122290e3a
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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