Sodium hydride → HCID 3822419, compound

HRID 1796117Notes

Reaction equation

HRID 1796117 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[H-].[Na+].I[CH2:13][C:14]1[N:18](S(C)(=O)=O)[C:17]2[CH:23]=[CH:24][CH:25]=[CH:26][C:16]=2[N:15]=1>CN(C)C=O.O>[NH:15]1[C:16]2[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=2[N:18]=[C:14]1[CH2:13][N:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1]1.[N:15]1[C:16]2[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=2[NH:18][C:14]=1[CH2:13][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 221814772-(Iodomethyl)-1-(methanesulfonyl)-1H-benzimidazoleHCID 178418385HCID 178418385, compound

Product 2

HCID 3822419HCID 3822419, compoundYield 48%HCID 13678006HCID 13678006, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzotriazole (238 mg, 2 mmol) in 4 mL of anhydrous N,N-dimethylformamide was added sodium hydride (60% in mineral oil, 88 mg, 2.2 mmol). After stirring for 1 hour, 2-iodomethyl-1-methanesulfonyl benzimidazole (740 mg, 2.2 mmol) was added. The resulting solution was stirred for 6 hours, diluted with water, and extracted with diethyl ether. The combined extracts were dried over magnesium sulfate, and evaporated. To the residue was added 5 mL of methanol and hydrazine (0.5 mL), and stirred at 65° C. overnight. The solvent was evaporated and the residue was diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography (EtOAc: hexane=1:1 to 2:1) to give 24 mg (5%) of 2-(1H-benzimidazol-2-ylmethyl)-2H-benzotriazole (IV), and 240 mg (48%) of 1-(1-benzimidazol-2-ylmethyl)-1H-benzotriazole (III) as solids.

Workup

  1. stirringThe resulting solution was stirred for 6 hours
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customevaporated
  5. additionTo the residue was added 5 mL of methanol and hydrazine (0.5 mL)
  6. stirringstirred at 65° C. overnight
  7. customThe solvent was evaporated
  8. additionthe residue was diluted with water
  9. extractionextracted with ethyl acetate
  10. dry with materialThe combined extracts were dried over magnesium sulfate
  11. customevaporated
  12. customThe residue was purified by flash chromatography (EtOAc: hexane=1:1 to 2:1)

Sources & evidence

ORD record
ord-a257a1e9a8e44e8a9df5a8e491d9805d
Source dataset
uspto-grants-2006_04
Patent number
US07030140B2

Reaction notes

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