Ammonia → HCID 18379885, compound

HRID 2299141Notes

Reaction equation

HRID 2299141 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-])=O.[OH:13][CH2:14][CH2:15]Br.[Br:17]Br.N>CC(O)=O.[H][H].[Pd].C(O)(C)C.C(Cl)(Cl)Cl>[OH:13][CH2:14][CH2:15][N:10]1[C:6]2[C:5]([Br:17])=[C:4]([NH2:1])[CH:12]=[CH:11][C:7]=2[N:8]=[CH:9]1.[OH:13][CH2:14][CH2:15][N:8]1[C:7]2[CH:11]=[CH:12][C:4]([NH2:1])=[C:5]([Br:17])[C:6]=2[N:10]=[CH:9]1

Participants

9

Reactant 4

HCID 222AmmoniaHCID 71955-NitrobenzimidazoleHCID 108982-BromoethanolHCID 24408Bromine

Product 2

HCID 18379806HCID 18379806, compoundHCID 18379885HCID 18379885, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 178506449HCID 178506449, compoundCatalystHCID 176Acetic AcidSolvent2×HCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

A reaction of 5-nitrobenzimidazole (3.3 g, 20 mmol) and 2-hydroxyethyl bromide (2.2 ml, 31 mmol) in a procedure described in Example 9 produces a mixture of 1- and 3-(2-hydroxyethyl)-5-nitrobenzimidazole, which was converted to the corresponding amines in hydrogenation (H2/Pd-C). The amine mixture (3.4 g, 19 mmol) in 50 ml of AcOH was added solution of Br2 in AcOH until it produces a precipitation. The reaction mixture was concentrated in vacuo to provide a brown solid which was subjected to column chromatography (5% NH3 sat'd isopropanol/CHCl3) to provide 0.42 g (1.6 mmol) of 3-(2-hydroxyethyl)-4-bromo-5-aminobenzimidazole and 0.57 g (2.2 mmol, 11%) of 1-(2-hydroxyethyl)-4-bromo-5-aminobenzimidazole.

Workup

  1. customproduces
  2. customproduces
  3. customa precipitation
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customto provide a brown solid which

Sources & evidence

ORD record
ord-f7ccfd346624440b8cc71f7a5d1825f2
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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