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

HRID 860100노트

반응식

HRID 860100 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9fce7cc8ae9d49d881d744b77a11d1ed
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153872B2

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