Triethylamine → 8-Chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro imidazo[1,2-a]benzimidazole-5-carbaldehyde

HRID 1628948Notes

Reaction equation

HRID 1628948 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:14]4[C:19]([CH3:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=4[Cl:22])[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH2:23][OH:24])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:23]=[O:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=3[Cl:22])[CH2:12][CH2:13][N:7]21

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 57785983[8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl]methanol

Product 1

HCID 577862078-Chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro imidazo[1,2-a]benzimidazole-5-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of [8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl]methanol (163 mg, 0.426 mmol) and triethylamine (0.48 mL, 3.44 mmol) in dimethylsulfoxide (5.0 mL) was added sulfur trioxide-pyridine complex (0.44 g, 2.76 mmol) at room temperature. The mixture was stirred at room temperature for 24 hr. Aqueous sodium hydrogen carbonate was added dropwise to the reaction mixture at room temperature. The precipitated solid was collected by filtration. The solid was washed with water, 2-propanol and diisopropyl ether to give the title compound (140.8 mg, 0.37 mmol, 87%) as a pale yellow solid.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washThe solid was washed with water, 2-propanol and diisopropyl ether

Sources & evidence

ORD record
ord-beb6e5b0256743e6b7f420400c6cbff5
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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