Benzoyl chloride → HCID 68464265, compound

HRID 507212Notes

Reaction equation

HRID 507212 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:14]([F:16])=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([N:17]4[CH2:22][CH2:21][N:20]([C:33]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[O:40])[CH2:19][CH2:18]4)[C:14]([F:16])=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 68467472HCID 68467472, compound

Product 1

HCID 68464265HCID 68464265, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

72 mg of 1-(4-chloro-benzyl)-5-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1H-benzoimidazole (0.16 mmol) and 0.033 ml TEA (0.24 mmol) were dissolved in 1.5 ml dichloromethane and treated with 0.023 ml benzoylchloride (0.2 mmol). After 1.5 h of stirring at rt, the reaction mixture was diluted with dichloromethane, washed with water, saturated sodium bicarbonate and brine, dried with magnesium sulfate, filtered and concentrated in vacuo, leading to 84 mg residue which was purified by column chromatography (9 g silicagel, ethylacetate/heptane 2:1). 69 mg product as a light yellow solid (98%) was obtained. MS (ISP) 555.3 (M+H)+.

Workup

  1. washwashed with water, saturated sodium bicarbonate and brine
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customwas purified by column chromatography (9 g silicagel, ethylacetate/heptane 2:1)

Sources & evidence

ORD record
ord-403b6d7fc2774205903f3f0e6448d5ca
Source dataset
uspto-grants-2010_08
Patent number
US07786128B2

Reaction notes

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