Nitrogen → 475648-88-5

HRID 1796338Notes

Reaction equation

HRID 1796338 reaction equation
N#N.[Cl:3][CH2:4][C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.[H-].[Na+]>C1COCC1>[N:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH:9][C:5]=1[CH2:4][N:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=[C:5]1[CH2:4][Cl:3]

Participants

5

Reactant 3

HCID 947NitrogenHCID 24758Sodium hydrideHCID 785712-Chloromethylbenzimidazole

Product 1

HCID 22181906475648-88-5Yield 22,165.699%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a three-necked, 12 L flask, flushed with N2, 2-(chloromethyl)benzimidazole (75 g, 0.45 mmol) and THF (10 L) were added, and the slurry was stirred for one hour at room temperature. Using an ice bath, the slurry was cooled to 0° C. and NaH (5.7 g, 95%, 0.23 mmol) was added. The slurry temperature increased to 4.5° C. The reaction mixture was stirred for 3 h and quenched with 150 g of silica gel. The slurry was concentrated to dryness under reduced pressure and purified using column chromatography (loaded with 40% EtOAc/hexanes, the eluting solvent started with 40% EtOAc/hexanes to end with 75% EtOAc/hexanes). 14.8 g of 1-benzimidazolylmethyl-2-(chloromethyl)benzimidazole 1 was obtained.

Workup

  1. additionwere added
  2. temperaturethe slurry was cooled to 0° C.
  3. temperatureThe slurry temperature increased to 4.5° C
  4. stirringThe reaction mixture was stirred for 3 h
  5. customquenched with 150 g of silica gel
  6. concentrationThe slurry was concentrated to dryness under reduced pressure
  7. custompurified

Sources & evidence

ORD record
ord-4a5619eda8944e29b6f60d472242921a
Source dataset
uspto-grants-2006_04
Patent number
US07030150B2

Reaction notes

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