Phosgene → HCID 76617664, compound

HRID 2105876Notes

Reaction equation

HRID 2105876 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:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[O:28][CH2:29][CH3:30])=[N:9]2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)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:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[O:28][CH2:29][CH3:30])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 68869780HCID 68869780, compound

Product 1

HCID 76617664HCID 76617664, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,5-Bis-(4-chloro-phenyl)-2-(4-cyano-2-ethoxy-phenyl)-4,5-dihydro-imidazole (1.25 g, 2.88 mmol, example 25) was dissolved in methylene chloride and diisopropylethylamine (2.41 mL, 13.8 mmol) was added. The mixture was cooled in an ice bath and phosgene (6.09 mL, 11.52 mmol, 20% in toluene) was added. The reaction mixture was stirred for 30 mm at ice temperature and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with a gradient of ethyl acetate in hexanes) gave 4,5-bis-(4-chloro-phenyl)-2-(4-cyano-2-ethoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride (1.35 g, 94%).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. concentrationconcentrated
  3. customPurification of the crude residue by flash column chromatography (silica gel
  4. washeluting with a gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7a8ba52cee7846bf84688790fe099dcc
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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