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

HRID 1633917

반응식

HRID 1633917 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3d46ad9a739e4d60a06b417c1322a365
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06503949B1

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