Acetic Acid → N-{[2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-4-yl]methyl}-N-methylethanamine

HRID 1698596Notes

Reaction equation

HRID 1698596 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([CH3:27])[C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=[C:14]([CH:15]=O)[C:7]=2[N:6]=1.[CH3:28][NH2:29].[C:30](O)(=O)[CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([CH3:27])[C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=[C:14]([CH2:15][N:29]([CH3:28])[CH2:30][CH3:31])[C:7]=2[N:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 580123672-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carbaldehyde

Product 1

HCID 58012323N-{[2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-4-yl]methyl}-N-methylethanamineYield 70%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carbaldehyde (120 mg, 0.296 mmol), methyl amine (2M tetrahydrofuran solution, 1.48 ml, 2.96 mmol), acetic acid (0.5 ml) and ethyl acetate (2.0 ml) was added sodium triacetoxyborohydride (314 mg, 1.48 mmol) and the reaction mixture was stirred at room temperature for 48 h. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on alumina with a 5% ethyl acetate/n-hexane to give 93 mg (0.21 mmol, 70%) of the title compound as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on alumina with a 5% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-55975ab50cd84e3ba97d5118720814af
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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