Potassium Carbonate → HCID 11786713, compound

HRID 277707Notes

Reaction equation

HRID 277707 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]([N:14]([CH2:20][C:21]1[N:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])[C:24]2[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=2[N:22]=1)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13].C([O-])([O-])=O.[K+].[K+].[Cl:44][CH2:45][CH2:46][CH2:47]I>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]([N:14]([CH2:20][C:21]1[N:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:47][CH2:46][CH2:45][Cl:44])[C:24]2[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=2[N:22]=1)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropaneHCID 9871407HCID 9871407, compound

Product 1

HCID 11786713HCID 11786713, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 350 mg (0.67 mmole) of (2-chloro-3,4-dimethoxyphenyl)-N-({l-[(2-hydroxyphenyl)methyl] benzimidazol-2-yl}methyl)-N-(3-methylbutyl) carboxamide and 278 mg (2.01 mmole) of K2CO3 in 2 mL of anhydrous N,N-dimethylformamide is treated with 79.1 μL (0.737 mmole) 1-chloro-3-iodo propane at room temperature for 19 hr. The resulting solution is diluted with 60 mL of ethyl acetate, washed with 3×20 mL water and 1×20 mL of brine, dried over anhydrous Na2SO4 and the solvent is removed in vacuo to afford 400 mg (99%) of (2-chloro-3,4-dimethoxyphenyl)-N-[(1-{[2-(3-chloropropoxy)phenyl]methyl}benzimidazol-2-yl)methyl]-N-(3-methylbutyl) carboxamide.

Workup

  1. washwashed with 3×20 mL water and 1×20 mL of brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-409c224910144366a7616095de26a00e
Source dataset
uspto-grants-2002_03
Patent number
US06358949B1

Reaction notes

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