Thionyl Chloride → 6-[Chloro-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one

HRID 2298988Notes

Reaction equation

HRID 2298988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)(O)[C:19]4[N:20]([CH3:24])[CH:21]=[N:22][CH:23]=4)[CH:16]=3)[N:11]([CH2:33][CH:34]3[CH2:36][CH2:35]3)[C:10](=[O:37])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:40])=O>ClCCl>[Cl:40][C:18]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)([C:19]1[N:20]([CH3:24])[CH:21]=[N:22][CH:23]=1)[C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:33][CH:34]1[CH2:36][CH2:35]1)[C:10](=[O:37])[CH:9]=[C:8]2[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 99149464-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one

Product 1

HCID 183790276-[Chloro-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-Chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one (2.3 g, 4.35 mmol) in dichloromethane (60 mL) at 0° C. was treated with thionyl chloride (15 mL). The reaction mixture was warmed to room temperature, stirred for 1 hour, heated to 45° C., and stirred for an additional hour. The mixture was cooled to ambient temperature and concentrated in vacuo to give 6-[Chloro-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one; hydrochloride (2.15 g, 85%) as a bright yellow powder.

Workup

  1. temperatureheated to 45° C.
  2. stirringstirred for an additional hour
  3. temperatureThe mixture was cooled to ambient temperature
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cffa23bd2884dfd983b031a1ccbd079
Source dataset
uspto-grants-2002_12
Patent number
US06495564B1

Reaction notes

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