Methanol → HCID 19094244, compound

HRID 487189Notes

Reaction equation

HRID 487189 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O.B#B.CO>O1CCCC1>[CH2:3]([C:4]1[N:9]([CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:10]2[C:11]([CH2:12][OH:14])=[CH:15][CH:16]=[CH:17][C:18]=2[N:19]=1)[CH2:2][CH2:7][CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 6328200DiboronHCID 19094224HCID 19094224, compound

Product 1

HCID 19094244HCID 19094244, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazole-7-carboxylic acid (Example 3) (9.06 g, 26.4 mmol) in dry tetrahydrofuran (950 mL) under an argon atmosphere was treated dropwise with a solution of diborane in tetrahydrofuran (105.2 mL of 1M diborane). The mixture was stirred at ambient temperature overnight. The reaction was cooled, treated with excess methanol continuously and the solvents were evaporated. The residue was dissolved in methylene chloride, and the solution was washed well with water, dried and concentrated. The crude product was chromatographed over 500 g of silica gel with a gradient of methanol in methylene chloride to give about 5 g of product. This was boiled in 10% hydrochloric acid (100 mL) and then chilled. The yellow crystals were filtered to provide 4.78 g of 2-n-butyl-1-(2-chlorophenyl)methyl-7-hydroxymethyl-1H-benzimidazole hydrochloride; mp 223°-233.5° C.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvents were evaporated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washthe solution was washed well with water
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was chromatographed over 500 g of silica gel with a gradient of methanol in methylene chloride

Sources & evidence

ORD record
ord-79098d79413049dfac1fc56a2dba738b
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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