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Diisopropylamine → 1-Amino-1-phenyl-2-(4,5-dimethylthiazol-2-yl)ethylene

HRID 341765
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HRID 341765 반응식
[CH3:1][C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[CH:9]([NH-:12])([CH3:11])C.[Li+].[CH2:14]([Li])[CH2:15][CH2:16][CH3:17].[CH:19](NC(C)C)(C)C>C1COCC1.C(#N)C1C=CC=CC=1>[NH2:12][C:9]([C:11]1[CH:19]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[CH:1][C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1
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참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 616532,4,5-TrimethylthiazoleHCID 10877046Lithium isopropylamideHCID 178418339Butyllithium

생성물 1

HCID 702759221-Amino-1-phenyl-2-(4,5-dimethylthiazol-2-yl)ethylene수율 76%

시약·촉매·용매 2

HCID 7505Benzonitrile
용매
HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

A solution of 5 g of 2,4,5-trimethylthiazol in 10 cm3 of anhydrous THF is added at -78° C. to a solution of 4.6 g of lithium isopropylamide, prepared in situ by adding 27 cm3 of n-butyllithium (1.6 M solution in hexane) to a solution of 4.35 g of diisopropylamine in 60 cm3 of anhydrous THF. After about 60 minutes a solution of 5.26 g of benzonitrile in 50 cm3 of anhydrous THF is slowly added dropwise, the temperature being maintained at -78° C. for a further 90 minutes. The temperature is left to rise slowly and the mixture is then left under stirring for a night. The solvent is evaporated, and ethyl acetate is added. The organic phase is washed with water, dried on sodium sulphate and is then evaporated. The raw product is purified on silica gel, using a mixture of ethyl acetate/hexane as eluant in a ratio of 3/7. 6.8 g of 1-amino-1-phenyl-2-(4,5-dimethylthiazol-2-yl)ethylene are obtained (yield 76%).

후처리

  1. customprepared in situ
  2. waitThe temperature is left
  3. waitthe mixture is then left
  4. customThe solvent is evaporated
  5. additionethyl acetate is added
  6. washThe organic phase is washed with water
  7. customdried on sodium sulphate
  8. customis then evaporated
  9. customThe raw product is purified on silica gel
  10. additiona mixture of ethyl acetate/hexane as eluant in a ratio of 3/7

출처 및 근거

ORD 기록
ord-5886ff7d1b30442abb82090c7fdd8a30
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05856311

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