HCID 13771317, compound → HCID 178441567, compound

HRID 1032553Notes

Reaction equation

HRID 1032553 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14]>C(O)(=O)CCCC>[CH2:3]([C:4]1[NH:1][C:2]2[C:3]([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=2[N:8]=1)[CH2:2][CH2:7][CH3:6]

Participants

3

Reactant 1

HCID 13771317HCID 13771317, compound

Product 1

HCID 178441567HCID 178441567, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 7991Pentanoic AcidSolvent

Procedure

500 mg of N-[2-(2,3-diamino-4-methoxyphenyl)ethyl]-N,N-dimethylamine is heated with 10 ml of valeric acid for 7 hours to 120° C. The reaction mixture is concentrated. The residue is taken up in diethyl ether and extracted with 4N hydrochloric acid. The aqueous phase is neutralized with potassium bicarbonate solution and extracted with ethyl acetate. The organic phase is dried with sodium sulfate and concentrated, thus producing 170 mg of 2-butyl-7-methoxy-4-[2-(N,N-dimethylamino)ethyl]benzimidazole, mp 116°-122° C., after recrystallizing the residue from ethyl acetate.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with 4N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c8f2d08cfa94f8db8c8a7759334552b
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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