Styrene → Ethyl 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylate

HRID 19756ノート

反応式

HRID 19756 の反応式
Cl[C:2](=[N:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C1C=CC=CC=1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([N:9]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8]2)=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 7501StyreneHCID 8471TriethylamineHCID 2761323Ethyl 2-chloro-2-(2-(4-chlorophenyl)hydrazono)acetate

生成物 1

HCID 23730695Ethyl 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylate収率 94%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

Part B: To a stirred boiling solution of ethyl 2-chloro[(4-chlorophenyl) hydrazono]acetate (22.95 gram, 0.088 mol) and styrene (30.3 ml, 0.264 mol) in benzene (140 ml) is added triethylamine (34.3 ml, 0.247 mol) and the resulting solution is heated at reflux temperature for 1 hour. The resulting solution is cooled to room temperature and the formed precipitate is removed by filtration and washed with toluene. The filtrate is concentrated in vacuo and purified by flash chromatography (silica gel, dichloromethane) to give ethyl 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxylate (27.2 gram, 94% yield) as a syrup which slowly solidifies on standing. 1H-NMR (200 MHz, CDCl3): 1.38 (t, J=7 Hz, 3H), 3.06 (dd, J=18 and 7 Hz, 1H), 3.73 (dd, J=18 and 13 Hz, 1H), 4.33 (q, J=7 Hz, 2H), 5.38 (dd, J=13 and 7 Hz, 1H), 7.02 (br d, J=8 Hz, 2H), 7.08-7.40 (m, 7H).

後処理

  1. temperaturethe resulting solution is heated
  2. temperatureat reflux temperature for 1 hour
  3. customthe formed precipitate is removed by filtration
  4. washwashed with toluene
  5. concentrationThe filtrate is concentrated in vacuo
  6. custompurified by flash chromatography (silica gel, dichloromethane)

出典と根拠

ORDレコード
ord-b81f9a52c9ce43eeae8ee4705c5ccc21
出典データセット
uspto-grants-2010_06
特許番号
US07745476B2

反応ノート

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