Phosgene → 4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 31507Notes

Reaction equation

HRID 31507 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=3[O:30][CH2:31][CH3:32])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:40](Cl)([Cl:42])=[O:41]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]([C:40]([Cl:42])=[O:41])[C:10]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][C:21]=3[O:30][CH2:31][CH3:32])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 101741684,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-1H-imidazole

Product 1

HCID 597928204,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl chlorideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-1H-imidazole (46 g, 95.97 mmol, example 1) and triethylamine (66.9 mL, 479.9 mmol) in methylene chloride (2 L) cooled to 0° C. was added phosgene (124.3 mL, 239.9 mmol, ˜20% solution in toluene) dropwise over a period of 30 min. The reaction mixture was stirred at room temperature for 1 h. Nitrogen gas was bubbled through the reaction mixture to remove excess phosgene. The reaction mixture was concentrated to dryness, and the residue was dried in vacuo for 1 h to give 4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride (51 g, 98% yield) as off-white solids. The product was used without further purification.

Workup

  1. customNitrogen gas was bubbled through the reaction mixture
  2. customto remove excess phosgene
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customthe residue was dried in vacuo for 1 h

Sources & evidence

ORD record
ord-f9887d6df49a4def8df6b1b0afd0b0d4
Source dataset
uspto-grants-2008_09
Patent number
US07425638B2

Reaction notes

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