2,5-Hexanedione → 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide

HRID 1185195ノート

反応式

HRID 1185195 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8])[NH:4][N:3]=1.[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:18][C:17]1[N:1]([C:2]2[CH:6]=[C:5]([C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8])[NH:4][N:3]=2)[C:14]([CH3:13])=[CH:15][CH:16]=1

参加物

5

反応物 2

HCID 80352,5-HexanedioneHCID 645248193-amino-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 866840463-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide収率 65%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 1140Toluene溶媒

実験手順

A 250-mL round-bottomed flask equipped with a magnetic stirrer and a Dean-Stark trap was charged with 150b (11.0 g, 1.0 eq., 64.7 mmol), hexane-2,5-dione (11.1 g, 1.5 eq., 97.2 mmol), p-toluenesulfonic acid monohydrate (558 mg, 0.05 eq., 3.24 mmol), and toluene (100 mL). The reaction mixture was refluxed overnight. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 1:2 petroleum ether/ethyl acetate to afford 150c (10.4 g, 65%) as a white solid. MS-ESI: [M+H]+ 249.0

後処理

  1. customA 250-mL round-bottomed flask equipped with a magnetic stirrer
  2. temperatureThe reaction mixture was refluxed overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica-gel column chromatography
  5. washeluting with 1:2 petroleum ether/ethyl acetate

出典と根拠

ORDレコード
ord-36e7a1ca11ef40c2b662d0e54055740e
出典データセット
uspto-grants-2014_03
特許番号
US08669251B2

反応ノート

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