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Dimethylformamide dimethyl acetal → methyl 1-(4-methoxyphenyl)-3-(morpholin-4-ylmethyl)-1H-pyrazole-4-carboxylate

HRID 2090923
ノート
印刷プレビュー

反応式

HRID 2090923 の反応式
[N:1]1([CH2:7][C:8](=O)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:15]OC(OC)N(C)C.Cl.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH2:33])=[CH:28][CH:27]=1>C(O)C>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:15]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:33]2)=[CH:28][CH:27]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 78373Dimethylformamide dimethyl acetalHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 15547736Methyl 4-(morpholin-4-yl)-3-oxobutanoate2 回

生成物 1

HCID 66778357methyl 1-(4-methoxyphenyl)-3-(morpholin-4-ylmethyl)-1H-pyrazole-4-carboxylate収率 93%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To methyl 4-(morpholin-4-yl)-3-oxobutanoate (7.0 g) synthesized in the above-mentioned (1) was added dimethylformamide-dimethylacetal (4.9 mL), and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, ethanol (200 mL) and 4-methoxyphenylhydrazine hydrochloride (6.3 g) were added, and the mixture was stirred at 100° C. for 3 hr. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (10.6 g, 93%) as a yellow oil.

後処理

  1. temperatureto cool to room temperature
  2. stirringthe mixture was stirred at 100° C. for 3 hr
  3. temperatureto cool to room temperature
  4. customthe solvent was evaporated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. concentrationThe extract was concentrated
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

出典と根拠

ORDレコード
ord-e56f9d67d3c54bd783c62f9dc3921b1d
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436043B2

反応ノート

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