Water → HCID 22156914, compound

HRID 1073806Notes

Reaction equation

HRID 1073806 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][C:6]1[NH:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1.[H-].[Na+].[CH2:18]([O:20][CH2:21][CH2:22]Cl)[CH3:19].O>CN(C)C=O>[CH2:18]([O:20][CH2:21][CH2:22][N:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]=[C:6]1[CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:15])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 24758Sodium hydrideHCID 22156921HCID 22156921, compound

Product 1

HCID 22156914HCID 22156914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Grams 6 2-(3-dimethylaminopropyl)benzimidazole in 100 ml N,N-dimethylformamide are treated with 1.8 g 60% sodium hydride, the mixture is warmed up to 60° C. and 4 g 2-ethoxyethyl chloride are added thereto. It is maintained at 60° C. for 5 hours, then it is poured into water, extracted with diethyl ether and the extracts washed thoroughly with water, filtered on charcoal, made anhydrous on sodium sulphate and evaporated to dryness. The residue is chromatographied on silica gel column eluting with chloroform:methyl alcohol (9:1) and it gives 1-(2-ethoxyethyl)-2-(3-dimethylaminopropyl)benzimidazole.

Workup

  1. temperatureIt is maintained at 60° C. for 5 hours
  2. extractionextracted with diethyl ether
  3. washthe extracts washed thoroughly with water
  4. filtrationfiltered on charcoal
  5. customevaporated to dryness
  6. washeluting with chloroform:methyl alcohol (9:1) and it

Sources & evidence

ORD record
ord-4cd7d27bf92a4b109cf5856453a37684
Source dataset
uspto-grants-1990_11
Patent number
US04971980

Reaction notes

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