Ammonia → 1H-Benzimidazole,2-(2-methoxyethyl)-(9CI)

HRID 344717Notes

Reaction equation

HRID 344717 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][O:10][CH2:11][CH2:12][C:13](O)=O.Cl.N>>[CH3:9][O:10][CH2:11][CH2:12][C:13]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 7243O-PhenylenediamineHCID 1344423-Methoxypropionic acid

Product 1

HCID 450782511H-Benzimidazole,2-(2-methoxyethyl)-(9CI)Yield 92%

Procedure

A mixture of 3.17 g (29.3 mmols) of o-phenylenediamine, 3.75 g (36.0 mmols) of 3-methoxypropionic acid [J. Am. Chem. Soc., 70, 1004 (1948)]and 32 ml of a 4 normal aqueous hydrochloric acid solution was heated under reflux for 14 hours. After cooling, the mixture was neutralized with a 28-30% aqueous ammonia solution. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol =20/1) to afford 4.74 g (yield: 92%) of 2-(2-methoxyethyl)benzimidazole.

Workup

  1. temperatureunder reflux for 14 hours
  2. temperatureAfter cooling
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol =20/1)

Sources & evidence

ORD record
ord-a5c94221b83146408507052e1ea5d85d
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

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