P-Toluenesulfonylhydrazide → 4-[(4-Cyclopropylcyclohexylamino)methyl]benzoic acid methyl ester

HRID 1633917

反応式

HRID 1633917 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]2[CH2:17][CH2:16][C:15](=[C:18]3[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1.C1(C)C=CC(S(NN)(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1

参加物

6

反応物 2

HCID 15303P-ToluenesulfonylhydrazideHCID 235501404-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester

生成物 1

HCID 235501394-[(4-Cyclopropylcyclohexylamino)methyl]benzoic acid methyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

4-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester (1.1 g, 3.9 mmol) was dissolved in DMF (40 mL) and p-toluenesulfonic acid hydrazide (2.8 g, 15.4 mmol) was added. The reaction was heated to 100° C. for 16 hours. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (75 mL) and water (40 mL) was added. The aqueous phase was extracted with ethyl acetate (25 mL) and the combined organic phases washed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (25 g silica) using heptane and ethyl acetate (1:1) as eluent to give 4-[(4-cyclopropylcyclohexylamino)methyl]benzoic acid methyl ester.

後処理

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. additionwas added
  3. extractionThe aqueous phase was extracted with ethyl acetate (25 mL)
  4. washthe combined organic phases washed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (25 g silica)

出典と根拠

ORDレコード
ord-3d46ad9a739e4d60a06b417c1322a365
出典データセット
uspto-grants-2003_01
特許番号
US06503949B1

関連ノート

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