Hydrochloric Acid → 4-Methoxybenzoylacetonitrile

HRID 489422

反応式

HRID 489422 の反応式
[C:1](#[N:3])[CH3:2].[C:4](OC)(=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.O.Cl>CS(C)=O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([CH2:2][C:1]#[N:3])=[O:13])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6342AcetonitrileHCID 8499Methyl anisate

生成物 1

HCID 2333984-Methoxybenzoylacetonitrile収率 79.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

To a solution of acetonitrile (15 g) in DMSO (25 mL) was added methyl p-anisate (25 g) and the mixture was stirred with heating at 60° C. for 1 hour. The reaction mixture was allowed to cool and cold water (100 mL) was added dropwise. The mixture was acidified with hydrochloric acid and the precipitated crystals were collected by filtration. The obtained crystals were extracted with ethyl acetate and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to give 4-methoxybenzoylacetonitrile (21 g) as colorless crystals. To a solution of the obtained crystals in toluene was added hydrazine monohydrate (13 g) and the mixture was heated under reflux for 3 hours. The mixture was cooled and the precipitated crystals were collected by filtration to give 5-amino-3-(4-methoxyphenyl)pyrazole (22 g). Subsequently, the title compound was prepared from methyl butyrate, 2-chlorobenzaldehyde and 5-amino-3-(4-methoxyphenyl)pyrazole in the same manner as in Example 94.

後処理

  1. temperatureto cool
  2. filtrationthe precipitated crystals were collected by filtration
  3. extractionThe obtained crystals were extracted with ethyl acetate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-e07b695f6a2b468c8b345565e55d4891
出典データセット
uspto-grants-2005_12
特許番号
US06977262B2

関連ノート

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