p-Toluenesulfonic acid → 1-(3-Chlorophenyl)-3-(4-methylphenyl)-2-(trichloromethyl)imidazolidine

HRID 971850Notes

Reaction equation

HRID 971850 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.O=[CH:20][C:21]([Cl:24])([Cl:23])[Cl:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][N:11]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[CH:20]2[C:21]([Cl:24])([Cl:23])[Cl:22])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6407ChloralHCID 21312028N~1~-(3-Chlorophenyl)-N~2~-(4-methylphenyl)ethane-1,2-diamine

Product 1

HCID 213120461-(3-Chlorophenyl)-3-(4-methylphenyl)-2-(trichloromethyl)imidazolidineYield 35.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture consisting of 12.2 gm of N-(3-chlorophenyl)-N'-(4-methyl-phenyl)-ethylenediamine, 9 gm of chloral, 100 ml of toluene and 1.2 gm of p-toluenesulfonic acid was heated at its boiling point for 45 minutes in a vessel equipped with a water trap. Thereafter, the reaction mixture was filtered while still hot, and the filtrate was evaporated in vacuo. The oily residue was allowed to cool and was then triturated with a little glacial acetic acid, whereupon crystallization occurred. The crystals were collected by suction filtration, washed with cold methanol, and recrystallized from ethanol, yielding 6.5 gm of the compound of the formula ##STR14## which had a melting point of 34°-36° C.

Workup

  1. temperaturewas heated at its boiling point for 45 minutes in a vessel
  2. customequipped with a water trap
  3. filtrationThereafter, the reaction mixture was filtered while still hot, and the filtrate
  4. customwas evaporated in vacuo
  5. temperatureto cool
  6. customwas then triturated with a little glacial acetic acid, whereupon crystallization
  7. filtrationThe crystals were collected by suction filtration
  8. washwashed with cold methanol
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-af4c44a9fa044ad18bbcfe8029d242ac
Source dataset
uspto-grants-1979_07
Patent number
US04161528

Reaction notes

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