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Sodium Azide → 2-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carbonyl azide

HRID 1295349
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HRID 1295349 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]1([CH:11]2[N:16]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:15][CH:14]3[C:12]2([C:27](Cl)=[O:28])[CH2:13]3)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.CC(C)=O>[C:5]1([CH:11]2[N:16]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)(=[O:18])=[O:19])[CH2:15][CH:14]3[C:12]2([C:27]([N:1]=[N+:2]=[N-:3])=[O:28])[CH2:13]3)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 589073242-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carbonyl chloride2회

생성물 1

HCID 589073212-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carbonyl azide수율 100.3%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매2회

실험 절차

To a stirred solution of sodium azide (5.63 g, 86.62 mmol) in 17 mL of water was added in a dropwise fashion to a solution of racemic 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carbonyl chloride (5.0 g, 13.3 mmol) (Intermediate 3) in 30 mL of acetone. 3 mL of water was then added to the reaction and the reaction mixture was stirred for 16 hours. The acetone was removed at reduced pressure and the reaction diluted with both methylene chloride and brine. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carbonyl azide (5.1 g, 100% crude yield).

후처리

  1. customThe acetone was removed at reduced pressure
  2. additionthe reaction diluted with both methylene chloride and brine
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-81fea920908648bd8f17c50b8a4bdf62
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07241798B2

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