Ammonium Chloride → (1-methyl-1H-1,3-benzodiazol-2-yl)methanol

HRID 576992

Reaction equation

HRID 576992 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]=[O:12].[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 344177(1-methyl-1H-1,3-benzodiazol-2-yl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 1-methyl-1H-benzimidazole-2-carbaldehyde (1.1 g, 6.8 mmol) in anhydrous methanol (50 mL) was added sodium borohydride (350 mg, 9.3 mmol). The reaction mixture was stirred at room temperature for 5 hours. Saturated ammonium chloride solution (20 mL) was added. Methanol was evaporated. The resultant mixture was extracted with EtOAc (3×50 mL) and CH2Cl2 (1×50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. (1-methyl-1H-benzimidazol-2-yl)methanol was obtained (1.1 g, 99% yield). The product was used without further purification.

Workup

  1. customMethanol was evaporated
  2. extractionThe resultant mixture was extracted with EtOAc (3×50 mL) and CH2Cl2 (1×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b23eeefdeb0146999159da3c67bbdb90
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Linked notes

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