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

HRID 268594

反応式

HRID 268594 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒HCID 22742125Tetrahydrofuran heptane ethylbenzol溶媒

反応条件

温度
0 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-aac106cf1a6c405b905ea34475681619
出典データセット
uspto-grants-2008_11
特許番号
US07446117B2

関連ノート

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