Phosgene → 5-(4-Chloro-phenyl)-4-cyclopentylmethyl-2-(2-ethoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 719141Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[O:21][CH2:22][CH3:23])=[N:10][CH:9]2[CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:37](Cl)([Cl:39])=[O:38]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:12]([C:37]([Cl:39])=[O:38])[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[O:21][CH2:22][CH3:23])=[N:10][CH:9]2[CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(4-chloro-phenyl)-4-cyclopentylmethyl-2-(2-ethoxy-4-methoxy-phenyl)-4,5-dihydro-1H-imidazole (160 mg, 0.387 mmol) in methylene chloride (15 mL) cooled to 0° C. were sequentially added triethylamine (108 μL, 0.774 mmol) and phosgene (589 μL, 1.161 mmol, 1.97 M in toluene). The reaction mixture was stirred at 0° C. under Argon for 30 min. The solvent and excess reagents were removed by rotovap, and the residue was purified by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel) eluting with 20–25% ethyl acetate in hexanes to give 5-(4-chloro-phenyl)-4-cyclopentylmethyl-2-(2-ethoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride (132.6 mg, 72%) as white solids.

Workup

customThe solvent and excess reagents were removed by rotovap
customthe residue was purified by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel)
washeluting with 20–25% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-28953dcf089240d8bb16e1821988d24a
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132421B2

Reaction notes

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