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Sodium Azide → 1h-Benzimidazole-1-carboxylic acid,4-(azidomethyl)-,1,1-dimethylethyl ester

HRID 393016
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HRID 393016 반응식
Br[CH2:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CC(C)=O.[I-].[Na+]>[N:19]([CH2:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[N+:20]=[N-:21]
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참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 15744964tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate

생성물 1

HCID 207147611h-Benzimidazole-1-carboxylic acid,4-(azidomethyl)-,1,1-dimethylethyl ester수율 84%

시약·촉매·용매 2

HCID 5238Sodium Iodide촉매HCID 180Acetone용매

실험 절차

A mixture of 4-(bromomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (1.08 g, 3.5 mmol), sodium azide (240 mg, 3.7 mmol), and sodium iodide (5 mg) in acetone (10 mL) was heated at reflux for 66 h. The solvent was evaporated and dichloromethane was added. The solution was washed with dilute aqueous sodium hydrogen carbonate, dried (Na2SO4), filtered and evaporated to give 4-(azidomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (800 mg, 84%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 66 h
  3. customThe solvent was evaporated
  4. additiondichloromethane was added
  5. washThe solution was washed with dilute aqueous sodium hydrogen carbonate
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-94eb8e16571d4c6aa790c03d9a01c95d
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06803384B2

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