Hydrochloric Acid → 4-Methoxybenzoylacetonitrile

HRID 489422

반응식

HRID 489422 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6342AcetonitrileHCID 8499Methyl anisate

생성물 1

HCID 2333984-Methoxybenzoylacetonitrile수율 79.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e07b695f6a2b468c8b345565e55d4891
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977262B2

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