2,4-Dimethoxybenzoyl chloride → HCID 9826690, compound

HRID 649893Notes

Reaction equation

HRID 649893 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[CH2:31][NH:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36]>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([N:32]([CH2:31][C:23]1[N:22]([CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH3:14])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=1)[CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:6]

Participants

4

Reactant 2

HCID 27347192,4-Dimethoxybenzoyl chlorideHCID 15546371HCID 15546371, compound

Product 1

HCID 9826690HCID 9826690, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.4 mmole 2-(chloromethyl)-1-[(2-methylphenyl)methyl]benzimidazole in 20 mL of dry Acetonitrile is treated with 10 mL of isoamylamine for 16 hr at room temperature. The solvent is removed in vacuo and the residue is partitioned between 30 mL of ethyl acetate and 10 mL of 1 N NaOH. The ethyl acetate layer is dried over anhydrous Na2SO4 and solvent removed in vacuo to afford 1.6 g 92% ({1-[(2-methylphenyl)methyl]benzimidazol-2-yl}methyl) (3-methylbutyl)amine. 2,4-dimethoxybenzoylchloride 1.5 eq is treated with 1.0 eq of ({1-[(2-methylphenyl)methyl]benzimidazol-2-yl}methyl) (3-methylbutyl)amine in dichloromethane at room temperature for 1 hr. The reaction is quenched with 1 N NaOH and partitioned between dichloromethane and water. The organic layer is dried with Na2SO4 and the solvent removed in vacuo. The residue is chromatographed (SiO2) with ethyl acetate to afford 95% of (2,4-dimethoxyphenyl)-N-({1-[(2-methylphenyl)methyl]benzimidazol-2-yl}methyl)-N-(3-methylbutyl)carboxamide (Compound 1). Mass Spec M+ 486.

Workup

  1. customThe reaction is quenched with 1 N NaOH
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic layer is dried with Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue is chromatographed (SiO2) with ethyl acetate

Sources & evidence

ORD record
ord-0a7166f967024db18b39637927520e06
Source dataset
uspto-grants-2001_08
Patent number
US06271241B1

Reaction notes

Loading…