Toluene → HCID 19066513, compound

HRID 481445Notes

Reaction equation

HRID 481445 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:25]([O:27]C)=O)[CH2:16][CH2:17][NH:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:11][CH:10]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][N:18]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[C:25]2=[O:27])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 19066512HCID 19066512, compound

Product 1

HCID 19066513HCID 19066513, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10 ml toluene solution of 4.54 g (14.8 mmol) of N-(4-chlorophenyl)-N-methoxycarbonyl-N'-(3-pyridyl)ethylenediamine in a 100 ml round-bottomed flask was heated gradually and, while distilling off toluene, it was heated for 1.5 hours at 190° to 210° C. The amorphous reaction mixture was cooled to room temperature and methylene chloride was added to dissolve. This was purified by column chromatography (silica gel, ethyl acetate:n-hexane=5:1) to obtain 2.28 g (yield 56%) of 1-(4-chlorophenyl)-3-(3-pyridyl)-2-imidazolidinone as brown crystals.

Workup

  1. distillationwhile distilling off toluene, it
  2. temperaturewas heated for 1.5 hours at 190° to 210° C
  3. customThe amorphous reaction mixture
  4. dissolutionto dissolve
  5. customThis was purified by column chromatography (silica gel, ethyl acetate:n-hexane=5:1)

Sources & evidence

ORD record
ord-8cb7123b25ec45109d7068f5cbdcd58a
Source dataset
uspto-grants-1998_08
Patent number
US05789425

Reaction notes

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