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Methylhydrazine → Farnesylamine

HRID 249125
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HRID 249125 반응식
[CH3:1][C:2]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])=[CH:3][CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.CNN.[OH-].[Na+]>C(O)C>[CH2:4]([NH2:5])[CH:3]=[C:2]([CH2:16][CH2:17][CH:18]=[C:19]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH3:26])[CH3:1]
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참가 물질

5

반응물 3

HCID 6061MethylhydrazineHCID 14798Sodium HydroxideHCID 542051882-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 3080630Farnesylamine수율 89%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution 2.50 g (7.1 mmol) of Part (1) compound in 15 ml of absolute ethanol at room temperature under argon was treated with 1.9 ml (35.57 mmol, 5.0 eq.) of methyl hydrazine and stirred for 2 hours at room temperature and 4 hours at reflux. After cooling and the addition of 7.1 ml (7.1 mmol, 1.0 eq.) of 1M NaOH, the ethanol was removed under reduced pressure. The residue was extracted with 350 ml of ethyl ether and the ether layer washed with 100 ml of lM NaOH, 50 ml of H2O and 50 ml of brine, dried (MgSO4) and evaporated to obtain 1.45 g of crude product. Purification by bulb-to-bulb distillation at 120° C./0.005 mm provided 1.405 g (89%) of title compound as a colorless oil.

후처리

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. customthe ethanol was removed under reduced pressure
  4. extractionThe residue was extracted with 350 ml of ethyl ether
  5. washthe ether layer washed with 100 ml of lM NaOH, 50 ml of H2O and 50 ml of brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto obtain 1.45 g of crude product
  9. customPurification
  10. distillationby bulb-to-bulb distillation at 120° C./0.005 mm

출처 및 근거

ORD 기록
ord-74dae765f8204675be713a5ad2f4aedb
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05212164

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