Water → HCID 178515267、化合物

HRID 654599ノート

反応式

HRID 654599 の反応式
[C:1]1([C:7]2[C:8]([NH2:12])=[N:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]1([N:19]2[C:23](=[O:24])[C:22](=O)[CH:21]([C:26](OCC)=[O:27])[CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>C(O)(=O)C.C(O)C>[CH:13]1([N:19]2[CH2:20][C:21]3[C:26](=[O:27])[N:9]4[N:10]=[CH:11][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[C:8]4[NH:12][C:22]=3[C:23]2=[O:24])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

6

反応物 3

HCID 962WaterHCID 28188294-Carbethoxy-1-cyclohexyl-2,3-dioxopyrrolidineHCID 178509246HCID 178509246、化合物

生成物 1

HCID 178515267HCID 178515267、化合物収率 51%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

実験手順

4-Phenylpyrazol-3-amine [Anderson, E. L. et al., "Synthesis . . . 3-Amino-4-Arylpyrazoles", J. Med. Chem., 7, (1964), pp. 259-268] (3.00 g, 18.8 mmole) and ethyl 1-cyclohexyl-4,5-dioxo-3-pyrrolidinecarboxylate (4.77 g, 18.8 mmole) were combined in glacial acetic acid (19 mL) and stirred under reflux for five hours. No precipitate was observed throughout the course of the reaction. Upon cooling, the reaction solidified to a light yellow mass which was dissolved in 95% ethanol (100 mL) at reflux and water (50 mL) was added slowly while maintaining reflux. After cooling to room temperature, the thick yellow solid was collected by suction filtration and washed with more ethanol/water. Drying under vacuum left 5.37 g homogenous by TLC. Unsatisfactory analysis prompted recrystallization from 95% ethanol (200 mL) to give 3.31 g (m.p.>148°, dec.). Yield: 51% of the subtitled compound. 1H NMR CDCl3, δ) 8.08 (s, 1H, pyrazole-H), 7.44 (d, 2H, J=8 Hz, 2-phenyl H), 7.36 (t, 2H, J=8 Hz, 3-phenyl H), 7.23 (t, 1H, J=8 Hz, 4-phenyl H), 4.37 (s, 2H, lactam CH2), 3.99 (m, 1H, cyclohexyl CH), 1.1-1.9 (m, 10H, chclohexyl CH2); IR (mull) 3519, 1692, 1638, 1613, 1455 cm-1 ; UV (ethanol) λmax(ε) 205 (29,400), 210sh (27,750), 237 (18,350), 268 (18,760), 370 (7700); MS m/e (rel. intens.) 349 (M+1, 23), 348 (M+, 97), 267 (18), 266 (100), 210 (8), 183 (9); Exact mass calc'd for C20H20N4O2 =348.1586; Found=348.1593; TLC (silica, 10% methanol/chloroform) Rf 0.52.

後処理

  1. customet al., "Synthesis
  2. temperatureunder reflux for five hours
  3. customNo precipitate was observed throughout the course of the reaction
  4. temperatureUpon cooling
  5. temperatureat reflux
  6. temperaturewhile maintaining
  7. temperaturereflux
  8. filtrationthe thick yellow solid was collected by suction filtration
  9. washwashed with more ethanol/water
  10. customDrying under vacuum
  11. waitleft 5.37 g homogenous by TLC
  12. customrecrystallization from 95% ethanol (200 mL)
  13. customto give 3.31 g (m.p.>148°, dec.)

出典と根拠

ORDレコード
ord-071c5195e52847a8aed773b344176d5f
出典データセット
uspto-grants-1992_07
特許番号
US05132424

反応ノート

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