Phosgene → 4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 645722

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[C:21]([O:26][CH2:27][CH3:28])=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:36](Cl)([Cl:38])=[O:37]>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:36]([Cl:38])=[O:37])[C:10]([C:20]3[C:21]([O:26][CH2:27][CH3:28])=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-1H-imidazole (475 mg, 1.152 mmol) and triethylamine (321 uL, 2.304 mmol) in methylene chloride (6 mL) cooled to 0° C. was added phosgene (895 uL, 1.728 mmol, 20% solution in toluene, Fluka). The reaction mixture was stirred at 0° C. for 30 min then concentrated to dryness. The residue was taken in ethyl acetate, and the solids were filtered off. The filtrate was concentrated to give crude 4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-imidazole-1-carbonyl chloride as yellow solids (450 mg).

Workup

concentrationthen concentrated to dryness
filtrationthe solids were filtered off
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-4955c73f8fd54948993b495cd9fa144b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705007B2

Linked notes

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