Sodium Azide → 1-Phenyl-cyclopropylamine

HRID 14056

반응식

HRID 14056 반응식
[N-:1]=[N+]=[N-].[Na+].[C:5]1([C:11]2(C(O)=O)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>S(=O)(=O)(O)O.ClCCl>[C:5]1([C:11]2([NH2:1])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 802061-Phenylcyclopropanecarboxylic acid

생성물 1

HCID 1945491-Phenyl-cyclopropylamine

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

Following the procedure described in N. W. Werner et. al., J. Org. Syn. Coll. Vol. 5, 273-276, sodium azide (0.915 g, 14.1 mmol) is slowly added to a solution of 1-phenyl-cyclopropanecarboxlic acid (1.0 g, 6.1 mmol) in concentrated sulfuric acid (5 ml) and dichloromethane (10 ml). The sodium sulfate precipitated out of solution. The reaction mixture is heated to 50 degrees C. for 17 hours and then cooled to 0 degrees C. The mixture is basified to pH=11 with sodium hydroxide (1N) and extracted with dichloromethane (2×). The organic layers are combined, dried over sodium sulfate, filtered and concentrated. The residue is purified by chromatography (silica gel; isopropyl alcohol/chloroform/ammonium hydroxide 4/95/1) to give the title compound, MS (ESI+) for C9H11N m/z (M+H)+=134.

후처리

  1. customThe sodium sulfate precipitated out of solution
  2. temperaturecooled to 0 degrees C
  3. extractionextracted with dichloromethane (2×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography (silica gel; isopropyl alcohol/chloroform/ammonium hydroxide 4/95/1)

출처 및 근거

ORD 기록
ord-b6b12c4b583a4f42ba7d7ac0bdcfa0de
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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