Triethylamine → Ethyl 1-(4-chloro-2-ethylphenylaminocarbonyl)cyclopropanecarboxylate

HRID 893205

반응식

HRID 893205 반응식
[C:1]([C:6]1([C:9]([OH:11])=O)[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].C(N(CC)CC)C.ClC(OCC)=O.[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[C:28]([CH2:33][CH3:34])[CH:27]=1>C(#N)C>[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:9]([C:6]2([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:7][CH2:8]2)=[O:11])=[C:28]([CH2:33][CH3:34])[CH:27]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 348714-Chloro-2-ethylanilineHCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

생성물 1

HCID 19096849Ethyl 1-(4-chloro-2-ethylphenylaminocarbonyl)cyclopropanecarboxylate수율 40%

시약·촉매·용매 1

HCID 6342Acetonitrile용매3회

실험 절차

To a stirred solution of 1.54 grams (0.01 mole) of 1-carboethoxycyclopropanecarboxylic acid (the monocarboxylic acid intermediate described in Example XVIII) and 0.99 gram (0.01 mole) of triethylamine in 75 milliliters of acetonitrile was added a solution of 1.06 grams (0.01 mole) of ethyl chloroformate in 25 milliliters of acetonitrile dropwise with cooling to 0° C.-5° C. After stirring at ice temperature for 30 minutes a solution of 1.52 grams (0.01 mole) of 4-chloro-2-ethylaniline in 20 milliliters of acetonitrile was fed dropwise with stirring and continued cooling. The reaction mixture was allowed to warm to room temperature, then stirred for approximately sixteen hours following which it was filtered and the filtrate freed of solvent by evaporation. The residue was dissolved in dichloromethane and extracted, successively, with water (2×50 milliliters), 2N HCl (2×50 milliliters) and water (1×50 milliliters). After drying (MgSO4), solvent was removed by evaporation and the solid recrystallized from hexane to give 1.15 grams (0.004 mole) of ethyl 1-(4-chloro-2-ethylphenylaminocarbonyl)cyclopropanecarboxylate as cream colored prisms having a melting point of 77° C.-80° C.

후처리

  1. temperaturewith cooling to 0° C.-5° C
  2. temperaturecontinued cooling
  3. stirringstirred for approximately sixteen hours
  4. filtrationwas filtered
  5. customthe filtrate freed of solvent by evaporation
  6. dissolutionThe residue was dissolved in dichloromethane
  7. extractionextracted
  8. dry with materialAfter drying (MgSO4), solvent
  9. customwas removed by evaporation
  10. customthe solid recrystallized from hexane

출처 및 근거

ORD 기록
ord-f370e5f079d2420890f13c7d8f75c678
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05123951

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