1,1'-Carbonyldiimidazole → 3-methyl-3H-benzotriazole-5-carboxylic acid methoxy-methyl-amide

HRID 860100Notes

Reaction equation

HRID 860100 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]([OH:13])=O)[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:27][NH:28][O:29][CH3:30]>CN(C)C=O>[CH3:30][O:29][N:28]([CH3:27])[C:11]([C:8]1[CH:9]=[CH:10][C:5]2[N:4]=[N:3][N:2]([CH3:1])[C:6]=2[CH:7]=1)=[O:13]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 178364261-methyl-1H-1,2,3-benzotriazole-6-carboxylic acid

Product 1

HCID 859571723-methyl-3H-benzotriazole-5-carboxylic acid methoxy-methyl-amideYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-3H-benzotriazole-5-carboxylic acid (1.67 g, 5.6 mmol) was suspended in 25 ml N,N-dimethylformamide. 1,1′-carbonyldiimidazole (1.0 g, 6.2 mmol) was added and the reaction stirred at room temperature for 90 minutes. Then, N,O-dimethylhydroxylamine hydrochloride (593 mg, 6.2 mmol) was added and the reaction stirred at room temperature overnight. The solvent was removed by rotary evaporation. The residue was dissolved in saturated aqueous ammonium chloride solution and extracted three times with chloroform. The combined organics were dried over sodium sulfate, filtered and concentrated to dryness. Crude material was purified on Biotage Flash 40S silica gel column using chloroform/methanol gradient system (100:0 to 97:3, respectively) as eluent to afford 3-methyl-3H-benzotriazole-5-carboxylic acid methoxy-methyl-amide (1.01 g, 82%).

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionThe residue was dissolved in saturated aqueous ammonium chloride solution
  4. extractionextracted three times with chloroform
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customCrude material was purified on Biotage Flash 40S silica gel column

Sources & evidence

ORD record
ord-9fce7cc8ae9d49d881d744b77a11d1ed
Source dataset
uspto-grants-2006_12
Patent number
US07153872B2

Reaction notes

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