Water → 4-Methyl-6-[4-(methylthio)phenyl]-2-pyridone

HRID 268594

반응식

HRID 268594 반응식
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]([CH3:15])=[CH:11][C:12](O)=[O:13].[CH3:16][S:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.O>CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C.C1COCC1.C(OCC)(=O)C>[CH3:9][C:10]1[CH:15]=[C:22]([C:21]2[CH:24]=[CH:25][C:18]([S:17][CH3:16])=[CH:19][CH:20]=2)[NH:23][C:12](=[O:13])[CH:11]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 109313-Methyl-2-butenoic acidHCID 5909604-(Methylthio)benzonitrileHCID 2724682Lithium diisopropylamide

생성물 1

HCID 586039744-Methyl-6-[4-(methylthio)phenyl]-2-pyridone수율 43%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매HCID 22742125Tetrahydrofuran heptane ethylbenzol용매

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온도
0 °C

실험 절차

To a stirred solution of lithium diisopropylamide (50 mL of a 2M solution in heptane/THF/ethyl benzene, 0.1 mol) in THF (50 mL) at −78° C. and under an atmosphere of nitrogen was added dropwise a solution of 3-methyl-2-butenoic acid (5 g, 0.05 mol) in THF (50 mL). The reaction was warmed to 0° C. for 30 minutes. After cooling to −78° C., a solution of 4-(methylthio)benzonitrile (7.45 g, 0.05 mol) in THF (50 mL) was added dropwise. Upon complete addition, the reaction was warmed to room temperature and stirred for 3 hours. Water (150 mL) and ethyl acetate (100 mL) were added to the reaction mixture and the resulting precipitate filtered, washed with ethyl acetate and dried to give the title compound (4.96 g, 43%) LC retention time 2.75 mins, MS m/z 232 (MH+).

후처리

  1. temperatureAfter cooling to −78° C.
  2. additionUpon complete addition
  3. temperaturethe reaction was warmed to room temperature
  4. filtrationthe resulting precipitate filtered
  5. washwashed with ethyl acetate
  6. customdried

출처 및 근거

ORD 기록
ord-aac106cf1a6c405b905ea34475681619
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446117B2

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