Sodium hydride → methyl 4-(benzotriazol-1-ylmethyl)benzoate

HRID 1019169Notes

Reaction equation

HRID 1019169 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.Br[CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1.[H-].[Na+]>CN(C=O)C.[NH4+].[Cl-]>[N:1]1([CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178418385HCID 178418385, compound

Product 1

HCID 2823339methyl 4-(benzotriazol-1-ylmethyl)benzoateYield 51.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of benzotriazole (1.14 g, 9.6 mmol) in DMF (25 mL) at 0° C. was added methyl 4-bromomethylbenzoate (2.22, 9.6 mmol) and NaH (12.25 mmol, 60% in oil). After stirring for 2 h, the mixture was diluted with aqueous NH4Cl, extracted with EtOAc. The EtOAc extract was washed H2O (3×), dried (MgSO4) and concentrated. The residue was chromatographed to give 1.32 g (51%) of the title compound as a white powder.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed H2O (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-4901d153868d47d180eec7099f001fae
Source dataset
uspto-grants-2002_11
Patent number
US06486142B2

Reaction notes

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