Pyridine → HCID 13881473, compound

HRID 1164463Notes

Reaction equation

HRID 1164463 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:21])[C:10]1=[NH:22].N1C=CC=CC=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCCl>[CH3:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=1[N:11]1[CH2:12][CH2:13][N:9]([C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[C:10]1=[N:22][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 112040802-Imidazolidinimine, 1,3-bis(2,6-dimethylphenyl)-

Product 1

HCID 13881473HCID 13881473, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 1.0 g (3.4 mmoles) of 1,3-bis(2',6'-dimethylphenyl)-2-imino-imidazolidine, prepared as described in Example 1, Method (a), 10 ml of 1,2-dichloroethane, 0.33 ml (0.32 g, 4.0 mmole) of dry pyridine and 0.46 ml (0.56 g, 4.0 mmoles) of benzoyl chloride is heated on a steam bath for 2 hours. The cooled mixture is washed thrice with 10 ml of water each, thrice with 10 ml of 10% aqueous sodium hydrogencarbonate solution each, and again thrice with 10 ml of water each, dried over anhydrous sodium sulfate, and the solvent is evaporated under reduced pressure. 1.0 g (74.1%) of crude 1,3-bis(2',6'-dimethylphenyl)-2-benzoylimino-imidazolidine are obtained. After recrystallization from aqueous methanol the product melts at 176°-178° C.

Workup

  1. customprepared
  2. temperatureis heated on a steam bath for 2 hours
  3. washThe cooled mixture is washed thrice with 10 ml of water each, thrice with 10 ml of 10% aqueous sodium hydrogencarbonate solution each, and again thrice with 10 ml of water each,
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-dd32e22108f74758a7d477e3ca0ef490
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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