Hydrochloric Acid → HCID 22485170, compound

HRID 2181052Notes

Reaction equation

HRID 2181052 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:13](OC)=[O:14].[BH4-].[Li+].Cl.C(Cl)(Cl)Cl>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:13][OH:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 4148881Lithium borohydride2×HCID 22485227HCID 22485227, compound

Product 1

HCID 22485170HCID 22485170, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-chloro-1,2-dimethyl-1H-benzimidazole-5-carboxylate (1.07 g) in anhydrous tetrahydrofuran (11 ml) was added portionwise lithium borohydride (198 mg) at room temperature and the mixture was stirred for 2 hr and heated to 60° C. Thereafter, lithium borohydride (99 mg) was added 3 times at 1 hr intervals. The reaction mixture was ice-cooled and adjusted to pH 2 with 1N hydrochloric acid. The mixture was stirred at room temperature for 30 min, and chloroform was added to the mixture. The precipitated crystals were collected by filtration to give 4-chloro-5-hydroxymethyl-1,2-dimethyl-1H-benzimidazole as colorless crystals (487 mg). The filtrate was extracted 6 times with chloroform:methanol=5:1. The organic layer was dried over anhydrous magnesium sulfate, filtrated and concentrated. The residue was crystallized from isopropyl ether to give the objective product as colorless crystals (417 mg).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-56ab40d9c98e4be2ba830620a1b90015
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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